1-(heterocyclic carbonyl) piperidines

ABSTRACT

The present invention relates to fungicidal 1-(heterocyclic carbonyl) piperidines and their thiocarbonyl derivatives, their process of preparation and intermediate compounds for their preparation, their use as fungicides, particularly in the form of fungicidal compositions and methods for the control of phytopathogenic fungi of plants using these compounds or their compositions.

The present invention relates to fungicidal 1-(heterocyclic carbonyl)piperidines and their thiocarbonyl derivatives, their process ofpreparation and intermediate compounds for their preparation, their useas fungicides, particularly in the form of fungicidal compositions andmethods for the control of phytopathogenic fungi of plants using thesecompounds or their compositions.

In international patent application DE3641343 certain fungicidalheterocyclylcarbonylimidazoles are generically embraced in a broaddisclosure of numerous compounds of the following formula:

wherein Y can represent a phenyl ring, n can be equal to 2 to 6, m canbe equal to 1 to 2, and R can represent various substituent among whicha methoxy group. However, there is no disclosure or suggestion in thisdocument of any such derivative wherein the imidazole moiety can bereplaced by a carbo-linked 5-membered heterocyclyl group.

In international patent application WO-2007/039781 certain inhibitors ofthe glutamate receptor are generically embraced in a broad disclosure ofnumerous compounds of the following formula:

wherein R can represent a heteroaryl group, Z can represent a —(CH₂)n-group where n can be 1 or 2, X₁ and X₂ are different and can be selectedfrom N or O, Q can be N or a —CH— group, and Y₁ and Y₂ can representvarious substituents. However, there is no disclosure or suggestion inthis document of any use of such derivatives as antifungal orantimicrobial compounds.

In international patent application WO-2007/039782 certain inhibitors ofthe glutamate receptor are generically embraced in a broad disclosure ofnumerous compounds of the following formula:

wherein R can represent a heteroaryl group, Z can represent a —(CH₂)n-group where n can be 1 or 2, and Y₁ and Y₂ can represent varioussubstituents. However, there is no disclosure or suggestion in thisdocument of any use of such derivatives as antifungal or antimicrobialcompounds.

It is always of high interest in the field of agrochemicals to usepesticidal compounds more active than the compounds already known by theman ordinary skilled in the art whereby reduced amounts of compound canbe used whilst retaining equivalent efficacy.

Furthermore, the provision of new pesticidal compounds with a higherefficacy strongly reduces the risk of appearance of resistant strains inthe fungi to be treated.

We have now found a new family of compounds which show enhancedfungicidal activity over the general known family of such compounds.

Accordingly, the present invention provides a 1-(heterocyclic[thio]carbonyl) piperidine derivative of formula (I)

wherein

-   -   A represents a carbo-linked, unsaturated or partially saturated,        5-membered heterocyclyl group that can be substituted by up to        four groups R that can be the same or different;    -   T represents O or S;    -   n represents 0, 1 or 2;    -   Q¹ represents a bond; O; S; SO; or SO₂;    -   B represents a phenyl ring that can be substituted by up to 5        groups X which can be the same or different; a naphthyl ring        that can be substituted by up to 7 groups X which can be the        same or different; or a saturated, partially saturated or        unsaturated, monocyclic or fused bicyclic 4-, 5-, 6-, 7-, 8-,        9-, 10-membered ring comprising from 1 up to 4 heteroaroms        selected in the list consisting of N, O, S, that can be        substituted by up to 6 groups X which can be the same or        different;    -   X represents a halogen atom; nitro; cyano; isonitrile; hydroxy;        amino; sulfanyl; pentafluoro-λ⁶-sulfanyl; formyl; formyloxy;        formylamino; substituted or non-substituted        (hydroxyimino)-C₁-C₈-alkyl; substituted or non-substituted        (C₁-C₈-alkoxyimino)-C₁-C₈-alkyl; substituted or non-substituted        (C₂-C₈-alkenyloxyimino)-C₁-C₈-alkyl; substituted or        non-substituted (C₂-C₈-alkynyloxyimino)-C₁-C₈-alkyl; substituted        or non-substituted (benzyloxyimino)-C₁-C₈-alkyl; carboxy;        carbamoyl; N-hydroxycarbamoyl; carbamate; substituted or        non-substituted C₁-C₈-alkyl; C₁-C₈-halogenoalkyl having 1 to 5        halogen atoms; substituted or non-substituted C₂-C₈-alkenyl;        C₂-C₈-halogenoalkenyl having 1 to 5 halogen atoms; substituted        or non-substituted C₂-C₈-alkynyl; C₂-C₈-halogenoalkynyl having 1        to 5 halogen atoms; substituted or non-substituted C₁-C₈-alkoxy;        C₁-C₈-halogenoalkoxy having 1 to 5 halogen atoms; substituted or        non-substituted C₁-C₈-alkylsulfanyl; C₁-C₈-halogenoalkylsulfanyl        having 1 to 5 halogen atoms; substituted or non-substituted        C₁-C₈-alkylsulfinyl; C₁-C₈-halogenoalkylsulfinyl having 1 to 5        halogen atoms; substituted or non-substituted        C₁-C₈-alkylsulfonyl; C₁-C₈-halogenoalkylsulfonyl having 1 to 5        halogen atoms; substituted or non-substituted C₁-C₈-alkylamino;        substituted or non-substituted di-C₁-C₈-alkylamino; substituted        or non-substituted C₂-C₈-alkenyloxy; C₂-C₈-halogenoalkenyloxy        having 1 to 5 halogen atoms; substituted or non-substituted        C₃-C₈-alkynyloxy; C₂-C₈-halogenoalkynyloxy having 1 to 5 halogen        atoms; substituted or non-substituted C₃-C₇-cycloalkyl;        C₃-C₇-halogenocycloalkyl having 1 to 5 halogen atoms;        substituted or non-substituted (C₃-C₇-cycloalkyl)-C₁-C₈-alkyl;        substituted or non-substituted (C₃-C₇-cycloalkyl)-C₂-C₈-alkenyl;        substituted or non-substituted (C₃-C₇-cycloalkyl)-C₂-C₈-alkynyl;        substituted or non-substituted tri(C₁-C₈)alkylsilyl; substituted        or non-substituted tri(C₁-C₈)alkylsilyl-C₁-C₈-alkyl; substituted        or non-substituted C₁-C₈-alkylcarbonyl;        C₁-C₈-halogenoalkylcarbonyl having 1 to 5 halogen atoms;        substituted or non-substituted C₁-C₈-alkylcarbonyloxy;        C₁-C₈-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms;        substituted or non-substituted C₁-C₈-alkylcarbonylamino;        C₁-C₈-halogenoalkyl-carbonylamino having 1 to 5 halogen atoms;        substituted or non-substituted C₁-C₈-alkoxycarbonyl;        C₁-C₈-halogenoalkoxycarbonyl having 1 to 5 halogen atoms;        substituted or non-substituted C₁-C₈-alkyloxycarbonyloxy;        C₁-C₈-halogenoalkoxycarbonyloxy having 1 to 5 halogen atoms;        substituted or non-substituted C₁-C₈-alkylcarbamoyl; substituted        or non-substituted di-C₁-C₈-alkylcarbamoyl; substituted or        non-substituted C₁-C₈-alkylaminocarbonyloxy; substituted or        non-substituted di-C₁-C₈-alkylaminocarbonyloxy; substituted or        non-substituted N—(C₁-C₈-alkyl)hydroxy carbamoyl; substituted or        non-substituted C₁-C₈-alkoxycarbamoyl; substituted or        non-substituted N—(C₁-C₈-alkyl)-C₁-C₈-alkoxycarbamoyl; aryl that        can be substituted by up to 6 groups Q which can be the same or        different; C₁-C₈-arylalkyl that can be substituted by up to 6        groups Q which can be the same or different; C₂-C₈-arylalkenyl        that can be substituted by up to 6 groups Q which can be the        same or different; C₂-C₈-arylalkynyl that can be substituted by        up to 6 groups Q which can be the same or different; aryloxy        that can be substituted by up to 6 groups Q which can be the        same or different; arylsulfanyl that can be substituted by up to        6 groups Q which can be the same or different; arylamino that        can be substituted by up to 6 groups Q which can be the same or        different; C₁-C₈-arylalkyloxy that can be substituted by up to 6        groups Q which can be the same or different;        C₁-C₈-arylalkylsulfanyl that can be substituted by up to 6        groups Q which can be the same or different; or        C₁-C₈-arylalkylamino that can be substituted by up to 6 groups Q        which can be the same or different; or    -   two substituent X together with the consecutive carbon atoms to        which they are linked can form a 5- or 6-membered, saturated        carbocycle or saturated heterocycle, which can be substituted by        up to four groups Q which can be the same or different;    -   Z¹ and Z² independently represent a hydrogen atom; a halogen        atom; cyano; substituted or non-substituted C₁-C₈-alkyl;        C₁-C₈-halogenoalkyl having 1 to 5 halogen atoms; substituted or        non-substituted C₁-C₈-alkoxy; substituted or non-substituted        C₁-C₈-alkylsulfanyl; or substituted or non-substituted        C₁-C₈-alkoxycarbonyl; or    -   two substituents Z¹ and Z², together with the carbon atom to        which they are linked can form a 3-, 4-, 5- or 6-membered        saturated carbocycle that can be substituted by up to four        C₁-C₈-alkyl groups;    -   Z³ represents a hydrogen atom; or substituted or non-substituted        C₁-C₈-alkyl;    -   Q independently represents a halogen atom; cyano; nitro;        substituted or non-substituted C₁-C₈-alkyl; C₁-C₈-halogenoalkyl        having 1 to 9 halogen atoms that can be the same or different;        substituted or non-substituted C₁-C₈-alkoxy;        C₁-C₈-halogenoalkoxy having 1 to 9 halogen atoms that can be the        same or different; substituted or non-substituted        C₁-C₈-alkylsulfanyl; C₁-C₈-halogenoalkylsulfanyl having 1 to 9        halogen atoms that can be the same or different; substituted or        non-substituted tri(C₁-C₈)alkylsilyl; substituted or        non-substituted tri(C₁-C₈)alkylsilyl-C₁-C₈-alkyl; substituted or        non-substituted (C₁-C₈-alkoxyimino)-C₁-C₈-alkyl; substituted or        non-substituted (benzyloxyimino)-C₁-C₈-alkyl;    -   R independently represents hydrogen atom; halogen atom; nitro;        cyano; hydroxy; amino; sulfanyl; pentafluoro-λ⁶-sulfanyl;        substituted or non-substituted (C₁-C₈-alkoxyimino)-C₁-C₈-alkyl;        substituted or non-substituted (benzyloxyimino)-C₁-C₈-alkyl;        substituted or non-substituted C₁-C₈-alkyl; C₁-C₈-halogenoalkyl        having 1 to 5 halogen atoms; substituted or non-substituted        C₂-C₈-alkenyl; C₂-C₈-halogenoalkenyl having 1 to 5 halogen        atoms; substituted or non-substituted C₂-C₈-alkynyl;        C₂-C₈-halogenoalkynyl having 1 to 5 halogen atoms; substituted        or non-substituted C₁-C₈-alkoxy; C₁-C₈-halogenoalkoxy having 1        to 5 halogen atoms; substituted or non-substituted        C₁-C₈-alkylsulfanyl; C₁-C₈-halogenoalkylsulfanyl having 1 to 5        halogen atoms; substituted or non-substituted        C₁-C₈-alkylsulfinyl; C₁-C₈-halogenoalkylsulfinyl having 1 to 5        halogen atoms; substituted or non-substituted        C₁-C₈-alkylsulfonyl; C₁-C₈-halogenoalkylsulfonyl having 1 to 5        halogen atoms; substituted or non-substituted C₁-C₈-alkylamino;        substituted or non-substituted di-C₁-C₈-alkylamino; substituted        or non-substituted C₂-C₈-alkenyloxy; substituted or        non-substituted C₃-C₈-alkynyloxy; substituted or non-substituted        C₃-C₇-cycloalkyl; C₃-C₇-halogenocycloalkyl having 1 to 5 halogen        atoms; substituted or non-substituted tri(C₁-C₈)alkylsilyl;        substituted or non-substituted C₁-C₈-alkylcarbonyl;        C₁-C₈-halogenoalkylcarbonyl having 1 to 5 halogen atoms;        substituted or non-substituted C₁-C₈-alkoxycarbonyl;        C₁-C₈-halogenoalkoxycarbonyl having 1 to 5 halogen atoms;        substituted or non-substituted C₁-C₈-alkylcarbamoyl; substituted        or non-substituted di-C₁-C₈-alkylcarbamoyl; phenoxy;        phenylsulfanyl; phenylamino; benzyloxy; benzylsulfanyl; or        benzylamino;        as well as its salts, N-oxides, metal complexes, metalloid        complexes and optically active isomers provided that the        following compounds are excluded:

-   (2,5-dimethyl-3-furyl){2-[2-(3-methylphenyl)-2H-tetrazol-5-yl]piperidin-1-yl}methanone

-   (5-bromo-2-furyl){2-[2-(3-bromophenyl)-2H-tetrazol-5-yl]piperidin-1-yl}methanone

-   (5-bromo-2-furyl){2-[2-(3-chlorophenyl)-2H-tetrazol-5-yl]piperidin-1-yl}methanone

-   (5-bromo-2-furyl){2-[2-(3-methoxyphenyl)-2H-tetrazol-5-yl]piperidin-1-yl}methanone

-   (5-bromo-2-thienyl){2-[2-(3-chlorophenyl)-2H-tetrazol-5-yl]piperidin-1-yl}methanone

-   (5-methyl-2-furyl){2-[2-(3-methylphenyl)-2H-tetrazol-5-yl]piperidin-1-yl}methanone

-   {2-[2-(3,5-dichlorophenyl)-2H-tetrazol-5-yl]piperidin-1-yl}(5-methyl-2-furyl)methanone

-   {2-[2-(3,5-dimethoxyphenyl)-2H-tetrazol-5-yl]piperidin-1-yl}(2-thienyl)methanone

-   {2-[2-(3-bromophenyl)-2H-tetrazol-5-yl]piperidin-1-yl}(2-furyl)methanone

-   {2-[2-(3-bromophenyl)-2H-tetrazol-5-yl]piperidin-1-yl}(2-thienyl)methanone

-   {2-[2-(3-bromophenyl)-2H-tetrazol-5-yl]piperidin-1-yl}(4,5-dimethyl-2-furyl)methanone

-   {2-[2-(3-bromophenyl)-2H-tetrazol-5-yl]piperidin-1-yl}(5-methyl-2-furyl)methanone

-   {2-[2-(3-bromophenyl)-2H-tetrazol-5-yl]piperidin-1-yl}(5-methyl-2-thienyl)methanone

-   {2-[2-(3-bromophenyl)-2H-tetrazol-5-yl]piperidin-1-yl}[5-(methylsulfanyl)-2-thienyl]methanone

-   {2-[2-(3-chlorophenyl)-2H-tetrazol-5-yl]piperidin-1-yl}(1,2,3-thiadiazol-4-yl)methanone

-   {2-[2-(3-chlorophenyl)-2H-tetrazol-5-yl]piperidin-1-yl}(1,3-dimethyl-1H-pyrazol-5-yl)methanone

-   {2-[2-(3-chlorophenyl)-2H-tetrazol-5-yl]piperidin-1-yl}(1,5-dimethyl-1H-pyrazol-3-yl)methanone

-   {2-[2-(3-chlorophenyl)-2H-tetrazol-5-yl]piperidin-1-yl}(2,4-dimethyl-1,3-thiazol-5-yl)methanone

-   {2-[2-(3-chlorophenyl)-2H-tetrazol-5-yl]piperidin-1-yl}(2-methyl-3-furyl)methanone

-   {2-[2-(3-chlorophenyl)-2H-tetrazol-5-yl]piperidin-1-yl}(3-furyl)methanone

-   {2-[2-(3-chlorophenyl)-2H-tetrazol-5-yl]piperidin-1-yl}(4,5-dimethyl-2-furyl)methanone

-   {2-[2-(3-chlorophenyl)-2H-tetrazol-5-yl]piperidin-1-yl}(4-methoxy-3-thienyl)methanone

-   {2-[2-(3-chlorophenyl)-2H-tetrazol-5-yl]piperidin-1-yl}(4-methyl-1,3-thiazol-5-yl)methanone

-   {2-[2-(3-chlorophenyl)-2H-tetrazol-5-yl]piperidin-1-yl}(5-methyl-1,2-oxazol-3-yl)methanone

-   {2-[2-(3-chlorophenyl)-2H-tetrazol-5-yl]piperidin-1-yl}(5-methyl-2-thienyl)methanone

-   {2-[2-(3-chlorophenyl)-2H-tetrazol-5-yl]piperidin-1-yl}[5-(methylsulfanyl)-2-thienyl]methanone

-   {2-[2-(3-fluorophenyl)-2H-tetrazol-5-yl]piperidin-1-yl}(5-methyl-2-furyl)methanone

-   {2-[2-(3-fluorophenyl)-2H-tetrazol-5-yl]piperidin-1-yl}(5-methyl-2-thienyl)methanone

-   {2-[2-(3-methoxyphenyl)-2H-tetrazol-5-yl]piperidin-1-yl}(2-thienyl)methanone

-   {2-[2-(3-methylphenyl)-2H-tetrazol-5-yl]piperidin-1-yl}(3-methyl-2-thienyl)methanone

-   {2-[2-(3-methylphenyl)-2H-tetrazol-5-yl]piperidin-1-yl}(3-thienyl)methanone

-   {2-[2-(3-methylphenyl)-2H-tetrazol-5-yl]piperidin-1-yl}(5-methyl-2-thienyl)methanone

-   {2-[3-(3,4-dimethylphenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl}(3-methyl-2-thienyl)methanone

-   {2-[3-(3-chlorophenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl}(2-furyl)methanone

-   {2-[3-(3-chlorophenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl}(3-furyl)methanone

-   {2-[3-(3-methoxyphenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl}(2-thienyl)methanone

-   {2-[3-(3-methoxyphenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl}(5-methyl-2-thienyl)methanone

-   {2-[3-(3-methylphenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl}(2-thienyl)methanone

-   2-furyl{2-[2-(3-methylphenyl)-2H-tetrazol-5-yl]piperidin-1-yl}methanone

-   2-furyl{2-[3-(3-methoxyphenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl}methanone

-   2-furyl{2-[3-(3-methylphenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl}methanone

-   3-(5-{1-[(5-bromo-2-thienyl)carbonyl]piperidin-2-yl}-2H-tetrazol-2-yl)benzonitrile

-   3-(5-{1-[(5-methyl-2-thienyl)carbonyl]piperidin-2-yl}-1,2,4-oxadiazol-3-yl)benzonitrile

-   3-(5-{1-[(5-methyl-2-thienyl)carbonyl]piperidin-2-yl}-2H-tetrazol-2-yl)benzonitrile

-   3-[5-(1-{[5-(methylsulfanyl)-2-thienyl]carbonyl}piperidin-2-yl)-2H-tetrazol-2-yl]benzonitrile

-   3-{5-[1-(2-furoyl)piperidin-2-yl]-2H-tetrazol-2-yl}benzonitrile

-   3-{5-[1-(2-thienylcarbonyl)piperidin-2-yl]-2H-tetrazol-2-yl}benzonitrile

-   3-{5-[1-(3-furoyl)piperidin-2-yl]-1,2,4-oxadiazol-3-yl}benzonitrile

-   3-{5-[1-(3-furoyl)piperidin-2-yl]-2H-tetrazol-2-yl}benzonitrile

-   3-{5-[1-(4,5-dimethyl-2-furoyl)piperidin-2-yl]-2H-tetrazol-2-yl}benzonitrile

-   3-{5-[1-(5-methyl-2-furoyl)piperidin-2-yl]-2H-tetrazol-2-yl}benzonitrile

-   3-furyl{2-[3-(3-methylphenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl}methanone

For the compounds according to the invention, the following genericterms are generally used with the following meanings:

-   -   halogen means fluorine, bromine, chlorine or iodine.        -   carboxy means —C(═O)OH;        -   carbonyl means —C(═O)—;        -   carbamoyl means —C(═O)NH₂;        -   N-hydroxycarbamoyl means —C(═O)NHOH;        -   SO represents a sulfoxide group;        -   SO₂ represents a sulfone group;    -   an alkyl group, an alkenyl group and an alkynyl group as well as        moieties containing these terms, can be linear or branched;    -   the aryl moiety contained in an aryl group, an arylalkyl group,        an arylalkenyl group and an arylalkynyl group as well as        moieties containing these terms, can be a phenyl group that can        be substituted by up to 5 groups Q which can be the same or        different, a naphthyl group that can be substituted by up to 7        groups Q which can be the same or different or a pyridyl group        that can be substituted by up to 4 groups Q which can be the        same or different;    -   heteroatom means sulfur, nitrogen or oxygen.    -   in the case of an amino group or the amino moiety of any other        amino-comprising group, substituted by two substituent that can        be the same or different, the two substituent together with the        nitrogen atom to which they are linked can form a heterocyclyl        group, preferably a 5- to 7-membered heterocyclyl group, that        can be substituted or that can include other hetero atoms, for        example a morpholino group or piperidinyl group.    -   unless indicated otherwise, a group or a substituent that is        substituted according to the invention can be substituted by one        or more of the following groups or atoms: a halogen atom, a        nitro group, a hydroxy group, a cyano group, an amino group, a        sulfanyl group, a pentafluoro-λ⁶-sulfanyl group, a formyl group,        a formyloxy group, a formylamino group, a carbamoyl group, a        N-hydroxycarbamoyl group, a carbamate group, a        (hydroxyimino)-C₁-C₆-alkyl group, a C₁-C₈-alkyl, a        tri(C₁-C₈-alkyl)silyl-C₁-C₈-alkyl, C₁-C₈-cycloalkyl,        tri(C₁-C₈-alkyl)silyl-C₁-C₈-cycloalkyl, a C₁-C₈-halogenoalkyl        having 1 to 5 halogen atoms, a C₁-C₈-halogenocycloalkyl having 1        to 5 halogen atoms, a C₂-C₈-alkenyl, a C₂-C₈-alkynyl, a        C₂-C₈-alkenyloxy, a C₂-C₈-alkynyloxy, a C₁-C₈-alkylamino, a        di-C₁-C₈-alkylamino, a C₁-C₈-alkoxy, a C₁-C₈-halogenoalkoxy        having 1 to 5 halogen atoms, a C₁-C₈-alkylsulfanyl, a        C₁-C₈-halogenoalkylsulfanyl having 1 to 5 halogen atoms, a        C₂-C₈-alkenyloxy, a C₂-C₈-halogenoalkenyloxy having 1 to 5        halogen atoms, a C₃-C₈-alkynyloxy, a C₃-C₈-halogenoalkynyloxy        having 1 to 5 halogen atoms, a C₁-C₈-alkylcarbonyl, a        C₁-C₈-halogenoalkylcarbonyl having 1 to 5 halogen atoms, a        C₁-C₈-alkylcarbamoyl, a di-C₁-C₈-alkylcarbamoyl, a        N—C₁-C₈-alkyloxycarbamoyl, a C₁-C₈-alkoxycarbamoyl, a        N—C₁-C₈-alkyl-C₁-C₈-alkoxycarbamoyl, a C₁-C₈-alkoxycarbonyl, a        C₁-C₈-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, a        C₁-C₈-alkylcarbonyloxy, a C₁-C₈-halogenoalkylcarbonyloxy having        1 to 5 halogen atoms, a C₁-C₈-alkylcarbonylamino, a        C₁-C₈-halogenoalkylcarbonylamino having 1 to 5 halogen atoms, a        C₁-C₈-alkylaminocarbonyloxy, a di-C₁-C₈-alkylaminocarbonyloxy, a        C₁-C₈-alkyloxycarbonyloxy, a C₁-C₈-alkylsulfinyl, a        C₁-C₈-halogenoalkylsulfinyl having 1 to 5 halogen atoms, a        C₁-C₈-alkylsulfonyl, a C₁-C₈-halogenoalkylsulfonyl having 1 to 5        halogen atoms, a C₁-C₈-alkylaminosulfamoyl, a        di-C₁-C₈-alkylaminosulfamoyl, a (C₁-C₆-alkoxyimino)-C₁-C₆-alkyl,        a (C₁-C₆-alkenyloxyimino)-C₁-C₆-alkyl, a        (C₁-C₆-alkynyloxyimino)-C₁-C₆-alkyl, a 2-oxopyrrolidin-1-yl,        (benzyloxyimino)-C₁-C₆-alkyl, C₁-C₈-alkoxyalkyl,        C₁-C₈-halogenoalkoxyalkyl having 1 to 5 halogen atoms,        benzyloxy, benzylsulfanyl, benzylamino, phenoxy, phenylsulfanyl,        or phenylamino.

Any of the compounds of the present invention can exist in one or moreoptical or chiral isomer forms depending on the number of asymmetriccentres in the compound. The invention thus relates equally to all theoptical isomers and to their racemic or scalemic mixtures (the term“scalemic” denotes a mixture of enantiomers in different proportions)and to the mixtures of all the possible stereoisomers, in allproportions. The diastereoisomers and/or the optical isomers can beseparated according to the methods which are known per se by the manordinary skilled in the art.

Any of the compounds of the present invention can also exist in one ormore geometric isomer forms depending on the number of double bonds inthe compound. The invention thus relates equally to all geometricisomers and to all possible mixtures, in all proportions. The geometricisomers can be separated according to general methods, which are knownper se by the man ordinary skilled in the art. Any of the compounds ofthe present invention can also exist in one or more geometric isomerforms depending on the relative position (syn/anti or cis/trans) of thesubstituents of ring B. The invention thus relates equally to allsyn/anti (or cis/trans) isomers and to all possible syn/anti (orcis/trans) mixtures, in all proportions. The syn/anti (or cis/trans)isomers can be separated according to general methods, which are knownper se by the man ordinary skilled in the art.

Any of the compounds of formula (I) wherein X represents a hydroxy, asulfanyl group or an amino group may be found in its tautomeric formresulting from the shift of the proton of said hydroxy, sulfanyl oramino group. Such tautomeric forms of such compounds are also part ofthe present invention. More generally speaking, all tautomeric forms ofcompounds of formula (I) wherein X represents a hydroxy, a sulfanylgroup or an amino group, as well as the tautomeric forms of thecompounds which can optionally be used as intermediates in thepreparation processes and which will be defined in the description ofthese processes, are also part of the present invention.

Preferred compounds according to the invention are compounds of formula(I) wherein A is selected in the list consisting of:

-   -   a heterocycle of formula (A¹)

wherein:R¹ to R³ that can be the same or different represent a hydrogen atom; ahalogen atom; substituted or non-substituted C₁-C₅-alkyl;C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different; substituted or non-substituted C₁-C₅-alkoxy orC₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different;

-   -   a heterocycle of formula (A²)

wherein:R⁴ to R⁶ that can be the same or different represent a hydrogen atom; ahalogen atom; substituted or non-substituted C₁-C₅-alkyl;C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different; substituted or non-substituted C₁-C₅-alkoxy orC₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different;

-   -   a heterocycle of formula (A³)

wherein:R⁷ represents a hydrogen atom; a halogen atom; substituted ornon-substituted C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different; substituted ornon-substituted C₁-C₅-alkoxy or C₁-C₅-halogenoalkoxy comprising up to 9halogen atoms that can be the same or different;R⁸ represents a hydrogen atom or a substituted or non-substitutedC₁-C₅-alkyl;

-   -   a heterocycle of formula (A⁴)

wherein:R⁹ to R¹¹ that can be the same or different represent a hydrogen atom; ahalogen atom; substituted or non-substituted C₁-C₅-alkyl; amino;substituted or non-substituted C₁-C₅-alkoxy; substituted ornon-substituted C₁-C₅-alkylsulfanyl; C₁-C₅-halogenoalkyl comprising upto 9 halogen atoms that can be the same or different orC₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different;

-   -   a heterocycle of formula (A⁵)

wherein:R¹² and R¹³ that can be the same or different represent a hydrogen atom;a halogen atom; substituted or non-substituted C₁-C₅-alkyl; substitutedor non-substituted C₁-C₅-alkoxy; amino; C₁-C₅-halogenoalkyl comprisingup to 9 halogen atoms that can be the same or different orC₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different;R¹⁴ represents a hydrogen atom; a halogen atom; substituted ornon-substituted C₁-C₅-alkyl; substituted or non-substitutedC₁-C₅-alkoxy; amino; C₁-C₅-halogenoalkyl comprising up to 9 halogenatoms that can be the same or different or C₁-C₅-halogenoalkoxycomprising up to 9 halogen atoms that can be the same or different;

-   -   a heterocycle of formula (A⁶)

wherein:R¹⁵ represents a hydrogen atom; a halogen atom; a cyano; substituted ornon-substituted C₁-C₅-alkyl; substituted or non-substitutedC₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms thatcan be the same or different or C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different;R¹⁶ and R¹⁸ that can be the same or different represent a hydrogen atom;a halogen atom; substituted or non-substituted C₁-C₅-alkoxycarbonyl;substituted or non-substituted C₁-C₅-alkyl; C₁-C₅-halogenoalkoxycomprising up to 9 halogen atoms that can be the same or different orC₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different;R¹⁷ represent a hydrogen atom or substituted or non-substitutedC₁-C₅-alkyl;

-   -   a heterocycle of formula (A⁷)

wherein:R¹⁹ represents a hydrogen atom or a C₁-C₅-alkylR²⁰ to R²² that can be the same or different represent a hydrogen atom;a halogen atom; substituted or non-substituted C₁-C₅-alkyl orC₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different;

-   -   a heterocycle of formula (A⁸)

wherein:R²³ represents a hydrogen atom; a halogen atom; substituted ornon-substituted C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different;R²⁴ represents a hydrogen atom or substituted or non-substitutedC₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms thatcan be the same or different;

-   -   a heterocycle of formula (A⁹)

wherein:R²⁵ represents a hydrogen atom; a halogen atom; substituted ornon-substituted C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different;R²⁶ represents a hydrogen atom; substituted or non-substitutedC₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms thatcan be the same or different;

-   -   a heterocycle of formula (A¹⁰)

wherein:R²⁷ represents a hydrogen atom; a halogen atom; substituted ornon-substituted C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different;R²⁸ represents a hydrogen atom; a halogen atom; substituted ornon-substituted C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different; C₁-C₅-halogenoalkoxycomprising up to 9 halogen atoms that can be the same or different;amino; substituted or non-substituted C₁-C₅-alkylamino or substituted ornon-substituted di(C₁-C₅-alkyl)amino;

-   -   a heterocycle of formula (A¹¹)

wherein:R²⁹ represents a hydrogen atom; a halogen atom; substituted ornon-substituted C₁-C₅-alkyl; substituted or non-substitutedC₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms thatcan be the same or different or C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different;R³⁰ represents a hydrogen atom; a halogen atom; substituted ornon-substituted C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different; C₁-C₅-halogenoalkoxycomprising up to 9 halogen atoms that can be the same or different;amino; substituted or non-substituted C₁-C₅-alkylamino or substituted ornon-substituted di(C₁-C₅-alkyl)amino;

-   -   a heterocycle of formula (A¹²)

wherein:R³¹ represents a hydrogen atom or a substituted or non-substitutedC₁-C₅-alkylR³² represents a hydrogen atom; a halogen atom; substituted ornon-substituted C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different;R³³ represents a hydrogen atom; a halogen atom; a nitro; substituted ornon-substituted C₁-C₅-alkyl; substituted or non-substitutedC₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms thatcan be the same or different or C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different;

-   -   a heterocycle of formula (A¹³)

wherein:R³⁴ represents a hydrogen atom; a halogen atom; substituted ornon-substituted C₁-C₅-alkyl; substituted or non-substitutedC₃-C₅-cycloalkyl; C₁-C₅-halogenoalkyl comprising up to 9 halogen atomsthat can be the same or different; substituted or non-substitutedC₁-C₅-alkoxy; substituted or non-substituted C₂-C₅-alkynyloxy orC₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different;R³⁵ represents a hydrogen atom; a halogen atom; substituted ornon-substituted C₁-C₅-alkyl; a cyano; substituted or non-substitutedC₁-C₅-alkoxy; substituted or non-substituted C₁-C₅-alkylsulfanyl;C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atomsthat can be the same or different; amino; substituted or non-substitutedC₁-C₅-alkylamino or substituted or non-substituted di(C₁-C₅-alkyl)amino;R³⁶ represents a hydrogen atom or substituted or non-substitutedC₁-C₅-alkyl;

-   -   a heterocycle of formula (A¹⁴)

wherein:R³⁷ and R³⁸ that can be the same or different represent a hydrogen atom;a halogen atom; substituted or non-substituted C₁-C₅-alkyl;C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different; substituted or non-substituted C₁-C₅-alkoxy or asubstituted or non-substituted C₁-C₅-alkylsulfanyl;R³⁹ represents a hydrogen atom or substituted or non-substitutedC₁-C₅-alkyl;

-   -   a heterocycle of formula (A¹⁵)

wherein:R⁴⁰ and R⁴¹ that can be the same or different represent a hydrogen atom;a halogen atom; substituted or non-substituted C₁-C₅-alkyl orC₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different;

-   -   a heterocycle of formula (A¹⁶)

wherein:R⁴² and R⁴³ that can be the same or different represent a hydrogen atom;a halogen atom; substituted or non-substituted C₁-C₅-alkyl;C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different or amino;

-   -   a heterocycle of formula (A¹⁷)

wherein:R⁴⁴ and R⁴⁵ that can be the same or different represent a hydrogen atom;a halogen atom; substituted or non-substituted C₁-C₅-alkyl orC₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different;

-   -   a heterocycle of formula (A¹⁸)

wherein:R⁴⁷ represents a hydrogen atom; a halogen atom; substituted ornon-substituted C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different;R⁴⁶ represents a hydrogen atom; a halogen atom; substituted ornon-substituted C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different or substituted ornon-substituted C₁-C₅-alkylsulfanyl;

-   -   a heterocycle of formula (A¹⁹)

wherein:R⁴⁹ and R⁴⁸ that can be the same or different represent a hydrogen atom;a halogen atom; substituted or non-substituted C₁-C₅-alkyl; substitutedor non-substituted C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 9halogen atoms that can be the same or different or C₁-C₅-halogenoalkylcomprising up to 9 halogen atoms that can be the same or different;

-   -   a heterocycle of formula (A²⁹)

wherein:R⁵⁰ and R⁵¹ that can be the same or different represent a hydrogen atom;a halogen atom; substituted or non-substituted C₁-C₅-alkyl; substitutedor non-substituted C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 9halogen atoms that can be the same or different or C₁-C₅-halogenoalkylcomprising up to 9 halogen atoms that can be the same or different;

-   -   a heterocycle of formula (A²¹)

wherein:R⁵² represents a hydrogen atom; a halogen atom; substituted ornon-substituted C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different.

-   -   a heterocycle of formula (A²²)

wherein:R⁵³ represents a hydrogen atom; a halogen atom; substituted ornon-substituted C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different.

-   -   a heterocycle of formula (A²³)

wherein:R⁵⁴ and R⁵⁶ that can be the same or different represent a hydrogen atom;a halogen atom; substituted or non-substituted C₁-C₅-alkyl orC₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different;R⁵⁵ represents a hydrogen atom or substituted or non-substitutedC₁-C₅-alkyl;

-   -   a heterocycle of formula (A²⁴)

wherein:R⁵⁷ and R⁵⁹ that can be the same or different represent a hydrogen atom;a halogen atom; substituted or non-substituted C₁-C₅-alkyl orC₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different;R⁵⁸ represents a hydrogen atom or substituted or non-substitutedC₁-C₅-alkyl;

-   -   a heterocycle of formula (A²⁵)

wherein:R⁶⁰ and R⁶¹ that can be the same or different represent a hydrogen atom;a halogen atom; substituted or non-substituted C₁-C₅-alkyl orC₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different;R⁶² represents a hydrogen atom or substituted or non-substitutedC₁-C₅-alkyl;

-   -   a heterocycle of formula (A²⁶)

wherein:R⁶⁵ represents a hydrogen atom; a halogen atom; substituted ornon-substituted C₁-C₅-alkyl; substituted or non-substitutedC₃-C₅-cycloalkyl; C₁-C₅-halogenoalkyl comprising up to 9 halogen atomsthat can be the same or different; substituted or non-substitutedC₁-C₅-alkoxy; substituted or non-substituted C₂-C₅-alkynyloxy orC₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different;R⁶³ represents a hydrogen atom; a halogen atom; substituted ornon-substituted C₁-C₅-alkyl; a cyano; substituted or non-substitutedC₁-C₅-alkoxy; substituted or non-substituted C₁-C₅-alkylsulfanyl;C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atomsthat can be the same or different; amino; substituted or non-substitutedC₁-C₅-alkylamino or di(C₁-C₅-alkyl)amino;R⁶⁴ represents a hydrogen atom or substituted or non-substitutedC₁-C₅-alkyl.

More preferred compounds according to the invention are compounds offormula (I) wherein A is selected in the list consisting of A²; A⁶; A¹⁰and A¹³ as herein-defined.

Even more preferred compounds according to the invention are compoundsof formula (I) wherein A represents A¹³ wherein R³⁴ represents asubstituted or non-substituted C₁-C₅-alkyl, C₁-C₅-halogenoalkylcomprising up to 9 halogen atoms that can be the same or different;substituted or non-substituted C₁-C₅-alkoxy; R³⁵ represents a hydrogenatom or a halogen atom and R³⁶ represents a substituted ornon-substituted C₁-C₅-alkyl.

Even more preferred compounds according to the invention are compoundsof formula (I) wherein A represents A¹³ wherein R³⁴ representsC₁-C₅-alkyl, C₁-C₅-halogenoalkyl comprising up to 3 halogen atoms thatcan be the same or different; R³⁵ represents a hydrogen atom; a chlorineatom; or a fluorine atom; and R³⁶ represents a methyl.

Other preferred compounds according to the invention are compounds offormula (I) wherein T represents O.

Other preferred compounds according to the invention are compounds offormula (I) wherein n represents 0 or 1.

Other preferred compounds according to the invention are compounds offormula (I) wherein Q¹ represents a bond or an oxygen atom; other morepreferred compounds according to the invention are compounds of formula(I) wherein Q¹ represents a bond.

Other preferred compounds according to the invention are compounds offormula (I) wherein B represents a substituted or non-substituted phenylring; a substituted or non-substituted naphthyl ring; a substituted ornon-substituted pyridyl ring; a substituted or non-substituted thienylring; or a substituted or non-substituted benzothienyl ring. Morepreferred compounds according to the invention are compounds of formula(I) wherein B represents a substituted or non-substituted phenyl ring;other more preferred compounds according to the invention are compoundsof formula (I) wherein B represents a substituted or non-substitutednaphthyl ring.

Other preferred compounds according to the invention are compounds offormula (I) wherein X independently represents a halogen atom;substituted or non-substituted C₁-C₅-alkyl; C₁-C₈-halogenoalkylcomprising up to 9 halogen atoms that can be the same or different;substituted or non-substituted C₁-C₅-alkoxy or C₁-C₅-halogenoalkoxycomprising up to 9 halogen atoms that can be the same or different; orwherein two consecutive substituents X together with the phenyl ringform a substituted or non substituted 1,3-benzodioxolyl or1,4-benzodioxanyl ring.

Other preferred compounds according to the invention are compounds offormula (I) wherein Z¹ and Z² independently represents a hydrogen atom,a halogen, substituted or non-substituted C₁-C₈-alkyl or substituted ornon-substituted C₁-C₈-alkoxy.

Other preferred compounds according to the invention are compounds offormula (I) wherein Z³ represents a hydrogen atom.

The above mentioned preferences with regard to the substituents of thecompounds according to the invention can be combined in various manners.These combinations of preferred features thus provide sub-classes ofcompounds according to the invention. Examples of such sub-classes ofpreferred compounds according to the invention are:

-   -   preferred features of A with preferred features of T, Q¹, B, n,        Z¹ to Z³, X and/or R;    -   preferred features of T with preferred features of A, Q¹, B, n,        Z¹ to Z³, X and/or R;    -   preferred features of Q¹ with preferred features of A, T, B, n,        Z¹ to Z³, X and/or R;    -   preferred features of B with preferred features of A, T, Q¹, n,        Z¹ to Z³, X and/or R;    -   preferred features of n with preferred features of A, T, Q¹, B,        Z¹ to Z³, X and/or R;    -   preferred features of Z¹ with preferred features of A, T, Q¹, B,        n, Z¹, Z³, X and/or R;    -   preferred features of Z² with preferred features of A, T, Q¹, B,        n, Z¹, Z³, X and/or R;    -   preferred features of Z³ with preferred features of A, T, Q¹, B,        n, Z¹, Z², X and/or R;    -   preferred features of X with preferred features of A, T, Q¹, B,        n, Z¹, to Z³ and/or R;    -   preferred features of R with preferred features of A, T, Q¹, B,        n, Z¹ to Z³ and/or X;

In these combinations of preferred features of the substituents of thecompounds according to the invention, the said preferred features canalso be selected among the more preferred features of each of A, T, Q¹,B, n, Z¹, Z², Z³, X and R so as to form most preferred subclasses ofcompounds according to the invention.

The present invention also relates to a process for the preparation ofthe compound of formula (I). Thus, according to a further aspect of thepresent invention there is provided a process P1 for the preparation ofa compound of formula (I) as herein-defined and wherein T represents Oand that comprises reaction of a piperidine of formula (II) or one ofits salts:

wherein Z¹, Z², Z³, n, Q¹ and B are as herein-defined; with a carboxylicacid derivative of formula (III):

wherein A is as herein-defined and L¹ represents a leaving groupselected in the list consisting of a halogen atom, a hydroxyl group,—OR^(a), —OC(═O)R^(a), R^(a) being a substituted or non-substitutedC₁-C₆-alkyl, a substituted or non-substituted C₁-C₆-haloalkyl, a benzyl,4-methoxybenzyl or pentafluorophenyl group, or a group of formulaO—C(═O)A; in the presence of a catalyst and in the presence of acondensing agent in case L¹ represents a hydroxyl group, and in thepresence of an acid binder in case L¹ represents a halogen atom.

Piperidines of formula (II) wherein n is equal to 0 can be prepared bydeprotonation of N-Boc-piperidine and transmetallation of the anion by azinc salt followed by a palladium coupling with (het)aryl bromides andfurther Boc deprotection (Organic Letters (2008), 10 (17), 3923-3925).Piperidines of formula (II) wherein n is equal to 1 or 2 can be preparedby hydrogenation of the corresponding 2-(het)arylmethyl or2-(het)arylethylpyridine (Helvetica Chimica Acta (1954), 37, 2133).

Carboxylic acid derivatives of formula (III) can be prepared by knownprocesses.

In case L¹ represents a hydroxy group, the process according to thepresent invention is conducted in the presence of condensing agent.Suitable condensing agent may be selected in the non limited listconsisting of acid halide former, such as phosgene, phosphoroustribromide, phosphorous trichloride, phosphorous pentachloride,phosphorous trichloride oxide or thionyl chloride; anhydride former,such as ethyl chloroformate, methyl chloroformate, isopropylchloroformate, isobutyl chloroformate or methanesulfonyl chloride;carbodiimides, such as N,N′-dicyclohexylcarbodiimide (DCC) or othercustomary condensing agents, such as phosphorous pentoxide,polyphosphoric acid, N,N′-carbonyl-diimidazole,2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ),triphenylphosphine/tetrachloro-methane,4-(4,6-dimethoxy[1.3.5]-triazin-2-yl)-4-methylmorpholinium chloridehydrate, bromo-tripyrrolidinophosphoniumhexafluorophosphate orpropanephosphonic anhydride (T3P).

The process according to the present invention is conducted in thepresence of a catalyst. Suitable catalyst may be selected in the listconsisting of 4-dimethyl-aminopyridine, 1-hydroxy-benzotriazole ordimethylformamide.

In case L¹ represents a halogen atom, the process according to thepresent invention is conducted in the presence of an acid binder.Suitable acid binders for carrying out process P1 according to theinvention are in each case all inorganic and organic bases that arecustomary for such reactions. Preference is given to using alkalineearth metal, alkali metal hydride, alkali metal hydroxides or alkalimetal alkoxides, such as sodium hydroxide, sodium hydride, calciumhydroxide, potassium hydroxide, potassium tert-butoxide or otherammonium hydroxide, alkali metal carbonates, such as cesium carbonate,sodium carbonate, potassium carbonate, potassium bicarbonate, sodiumbicarbonate, alkali metal or alkaline earth metal acetates, such assodium acetate, potassium acetate, calcium acetateand also tertiaryamines, such as trimethylamine, triethylamine, diisopropylethylamine,tributylamine, N,N-dimethylaniline, pyridine, N-methylpiperidine,N,N-dimethylaminopyridine, diazabicyclooctane (DABCO),diazabicyclo-nonene (DBN) or diazabicycloundecene (DBU).

It is also possible to work in the absence of an additional condensingagent or to employ an excess of the amine component, so that itsimultaneously acts as acid binder agent.

According to a further aspect according to the invention, there isprovided a process P2 for the preparation of a compound of formula (I)wherein T represents S, starting from a compound of formula (I) whereinT represents O and illustrated according to the following reactionscheme:

wherein A, Z¹, Z², Z³, n, Q¹ and B are as herein-defined, in theoptionally presence of a catalytic or stoichiometric or excess amount,quantity of a base such as an inorganic and organic base. Preference isgiven to using alkali metal carbonates, such as sodium carbonate,potassium carbonate, potassium bicarbonate, sodium bicarbonate;heterocyclic aromatic bases, such as pyridine, picoline, lutidine,collidine; and also tertiary amines, such as trimethylamine,triethylamine, tributylamine, N,N-dimethylaniline,N,N-dimethylaminopyridine or N-methyl-piperidine.

Process P2 according to the invention is performed in the presence of athionating agent.

Starting amide derivatives of formula (I) can be prepared according toprocesses P1.

Suitable thionating agents for carrying out process P2 according to theinvention can be sulfur (S), sulfhydric acid (H₂S), sodium sulfide(Na₂S), sodium hydrosulfide (NaHS), boron trisulfide (B₂S₃),bis(diethylaluminium) sulfide ((AlEt₂)₂S), ammonium sulfide ((NH₄)₂S),phosphorous pentasulfide (P₂S₅), Lawesson's reagent(2,4-bis(4-methoxyphenyl)-1,2,3,4-dithiadiphosphetane 2,4-disulfide) ora polymer-supported thionating reagent such as described in Journal ofthe Chemical Society, Perkin 1 (2001), 358.

Work-up is carried out by customary methods. Generally, the reactionmixture is treated with water and the organic phase is separated offand, after drying, concentrated under reduced pressure. If appropriate,the remaining residue can, be freed by customary methods, such aschromatography, recrystallization or distillation, from any impuritiesthat may still be present.

The compound according to the present invention can be preparedaccording to the general processes of preparation described above. Itwill nevertheless be understood that, on the basis of his generalknowledge and of available publications, the skilled worker will be ableto adapt this method according to the specifics of each of thecompounds, which it is desired to synthesize.

In a further aspect, the present invention also relates to a fungicidecomposition comprising an effective and non-phytotoxic amount of anactive compound of formula (I).

The expression “effective and non-phytotoxic amount” means an amount ofcomposition according to the invention that is sufficient to control ordestroy the fungi present or liable to appear on the cropsand that doesnot entail any appreciable symptom of phytotoxicity for the said crops.Such an amount can vary within a wide range depending on the fungus tobe controlled, the type of crop, the climatic conditions and thecompounds included in the fungicide composition according to theinvention. This amount can be determined by systematic field trials thatare within the capabilities of a person skilled in the art.

Thus, according to the invention, there is provided a fungicidecomposition comprising, as an active ingredient, an effective amount ofa compound of formula (I) as herein defined and an agriculturallyacceptable support, carrier or filler.

According to the invention, the term “support” denotes a natural orsynthetic, organic or inorganic compound with that the active compoundof formula (I) is combined or associated to make it easier to apply,notably to the parts of the plant. This support is thus generally inertand should be agriculturally acceptable. The support can be a solid or aliquid. Examples of suitable supports include clays, natural orsynthetic silicates, silica, resins, waxes, solid fertilisers, water,alcohols, in particular butanol, organic solvents, mineral and plantoils and derivatives thereof. Mixtures of such supports can also beused.

The composition according to the invention can also comprise additionalcomponents. In particular, the composition can further comprise asurfactant. The surfactant can be an emulsifier, a dispersing agent or awetting agent of ionic or non-ionic type or a mixture of suchsurfactants. Mention can be made, for example, of polyacrylic acidsalts, lignosulfonic acid salts, phenolsulfonic or naphthalenesulfonicacid salts, polycondensates of ethylene oxide with fatty alcohols orwith fatty acids or with fatty amines, substituted phenols (inparticular alkylphenols or arylphenols), salts of sulfosuccinic acidesters, taurine derivatives (in particular alkyl taurates), phosphoricesters of polyoxyethylated alcohols or phenols, fatty acid esters ofpolyolsand derivatives of the above compounds containing sulfate,sulfonate and phosphate functions. The presence of at least onesurfactant is generally essential when the active compound and/or theinert support are water-insoluble and when the vector agent for theapplication is water. Preferably, surfactant content can be comprisedfrom 5% to 40% by weight of the composition.

Optionally, additional components can also be included, e.g. protectivecolloids, adhesives, thickeners, thixotropic agents, penetration agents,stabilisers, sequestering agents. More generally, the active compoundscan be combined with any solid or liquid additive, that complies withthe usual formulation techniques.

In general, the composition according to the invention can contain from0.05 to 99% by weight of active compound, preferably 10 to 70% byweight.

Compositions according to the invention can be used in various formssuch as aerosol dispenser, capsule suspension, cold fogging concentrate,dustable powder, emulsifiable concentrate, emulsion oil in water,emulsion water in oil, encapsulated granule, fine granule, flowableconcentrate for seed treatment, gas (under pressure), gas generatingproduct, granule, hot fogging concentrate, macrogranule, microgranule,oil dispersible powder, oil miscible flowable concentrate, oil miscibleliquid, paste, plant rodlet, powder for dry seed treatment, seed coatedwith a pesticide, soluble concentrate, soluble powder, solution for seedtreatment, suspension concentrate (flowable concentrate), ultra lowvolume (ULV) liquid, ultra low volume (ULV) suspension, waterdispersible granules or tablets, water dispersible powder for slurrytreatment, water soluble granules or tablets, water soluble powder forseed treatment and wettable powder. These compositions include not onlycompositions that are ready to be applied to the plant or seed to betreated by means of a suitable device, such as a spraying or dustingdevice, but also concentrated commercial compositions that must bediluted before application to the crop.

The compounds according to the invention can also be mixed with one ormore insecticide, fungicide, bactericide, attractant, acaricide orpheromone active substance or other compounds with biological activity.The mixtures thus obtained have normally a broadened spectrum ofactivity. The mixtures with other fungicide compounds are particularlyadvantageous.

Examples of suitable fungicide mixing partners can be selected in thefollowing lists:

(1) Inhibitors of the ergosterol biosynthesis, for example (1.1)aldimorph (1704-28-5), (1.2) azaconazole (60207-31-0), (1.3) bitertanol(55179-31-2), (1.4) bromuconazole (116255-48-2), (1.5) cyproconazole(113096-99-4), (1.6) diclobutrazole (75736-33-3), (1.7) difenoconazole(119446-68-3), (1.8) diniconazole (83657-24-3), (1.9) diniconazole-M(83657-18-5), (1.10) dodemorph (1593-77-7), (1.11) dodemorph acetate(31717-87-0), (1.12) epoxiconazole (106325-08-0), (1.13) etaconazole(60207-93-4), (1.14) fenarimol (60168-88-9), (1.15) fenbuconazole(114369-43-6), (1.16) fenhexamid (126833-17-8), (1.17) fenpropidin(67306-00-7), (1.18) fenpropimorph (67306-03-0), (1.19) fluquinconazole(136426-54-5), (1.20) flurprimidol (56425-91-3), (1.21) flusilazole(85509-19-9), (1.22) flutriafol (76674-21-0), (1.23) furconazole(112839-33-5), (1.24) furconazole-cis (112839-32-4), (1.25) hexaconazole(79983-71-4), (1.26) imazalil (60534-80-7), (1.27) imazalil sulfate(58594-72-2), (1.28) imibenconazole (86598-92-7), (1.29) ipconazole(125225-28-7), (1.30) metconazole (125116-23-6), (1.31) myclobutanil(88671-89-0), (1.32) naftifine (65472-88-0), (1.33) nuarimol(63284-71-9), (1.34) oxpoconazole (174212-12-5), (1.35) paclobutrazol(76738-62-0), (1.36) pefurazoate (101903-30-4), (1.37) penconazole(66246-88-6), (1.38) piperalin (3478-94-2), (1.39) prochloraz(67747-09-5), (1.40) propiconazole (60207-90-1), (1.41) prothioconazole(178928-70-6), (1.42) pyributicarb (88678-67-5), (1.43) pyrifenox(88283-41-4), (1.44) quinconazole (103970-75-8), (1.45) simeconazole(149508-90-7), (1.46) spiroxamine (118134-30-8), (1.47) tebuconazole(107534-96-3), (1.48) terbinafine (91161-71-6), (1.49) tetraconazole(112281-77-3), (1.50) triadimefon (43121-43-3), (1.51) triadimenol(89482-17-7), (1.52) tridemorph (81412-43-3), (1.53) triflumizole(68694-11-1), (1.54) triforine (26644-46-2), (1.55) triticonazole(131983-72-7), (1.56) uniconazole (83657-22-1), (1.57) uniconazole-p(83657-17-4), (1.58) viniconazole (77174-66-4), (1.59) voriconazole(137234-62-9), (1.60)1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)cycloheptanol (129586-32-9),(1.61) methyl1-(2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)-1H-imidazole-5-carboxylate(110323-95-0), (1.62)N′-{5-(difluoromethyl)-2-methyl-4-[3-(trimethylsilyl)propoxy]phenyl}-N-ethyl-N-methylimidoformamide,(1.63)N-ethyl-N-methyl-N′-{2-methyl-5-(trifluoromethyl)-4-[3-(trimethylsilyl)propoxy]phenyl}imidoformamideand (1.64)O-[1-(4-methoxyphenoxy)-3,3-dimethylbutan-2-yl]1H-imidazole-1-carbothioate(111226-71-2).(2) inhibitors of the respiratory chain at complex I or II, for example(2.1) bixafen (581809-46-3), (2.2) boscalid (188425-85-6), (2.3)carboxin (5234-68-4), (2.4) diflumetorim (130339-07-0), (2.5) fenfuram(24691-80-3), (2.6) fluopyram (658066-35-4), (2.7) flutolanil(66332-96-5), (2.8) fluxapyroxad (907204-31-3), (2.9) furametpyr(123572-88-3), (2.10) furmecyclox (60568-05-0), (2.11) isopyrazam(mixture of syn-racemate 1RS,4SR,9RS and anti-epimeric racemate1RS,4SR,9SR) (881685-58-1), (2.12) isopyrazam (anti-epimeric racemate1RS,4SR,9SR), (2.13) isopyrazam (anti-epimeric enantiomer 1R,4S,9S),(2.14) isopyrazam (anti-epimeric enantiomer 1S,4R,9R), (2.15) isopyrazam(syn epimeric racemate 1RS,4SR,9RS), (2.16) isopyrazam (syn-epimericenantiomer 1R,4S,9R), (2.17) isopyrazam (syn-epimeric enantiomer1S,4R,9S), (2.18) mepronil (55814-41-0), (2.19) oxycarboxin (5259-88-1),(2.20) penflufen (494793-67-8), (2.21) penthiopyrad (183675-82-3),(2.22) sedaxane (874967-67-6), (2.23) thifluzamide (130000-40-7), (2.24)1-methyl-N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide,(2.25)3-(difluoromethyl)-1-methyl-N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-1H-pyrazole-4-carboxamide,(2.26)3-(difluoromethyl)-N-[4-fluoro-2-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]-1-methyl-1H-pyrazole-4-carboxamide,(2.27)N-[1-(2,4-dichlorophenyl)-1-methoxypropan-2-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide(1092400-95-7) (WO 2008148570), (2.28)5,8-difluoro-N-[2-(2-fluoro-4-{[4-(trifluoromethyl)pyridin-2-yl]oxy}phenyl)ethyl]quinazolin-4-amine(1210070-84-0) (WO2010025451), (2.29)N-[9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.30)N-[(1S,4R)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamideand (2.31)N-[(1R,4S)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide.(3) inhibitors of the respiratory chain at complex III, for example(3.1) ametoctradin (865318-97-4), (3.2) amisulbrom (348635-87-0), (3.3)azoxystrobin (131860-33-8), (3.4) cyazofamid (120116-88-3), (3.5)coumethoxystrobin (850881-30-0), (3.6) coumoxystrobin (850881-70-8),(3.7) dimoxystrobin (141600-52-4), (3.8) enestroburin (238410-11-2) (WO2004/058723), (3.9) famoxadone (131807-57-3) (WO 2004/058723), (3.10)fenamidone (161326-34-7) (WO 2004/058723), (3.11) fenoxystrobin(918162-02-4), (3.12) fluoxastrobin (361377-29-9) (WO 2004/058723),(3.13) kresoxim-methyl (143390-89-0) (WO 2004/058723), (3.14)metominostrobin (133408-50-1) (WO 2004/058723), (3.15) orysastrobin(189892-69-1) (WO 2004/058723), (3.16) picoxystrobin (117428-22-5) (WO2004/058723), (3.17) pyraclostrobin (175013-18-0) (WO 2004/058723),(3.18) pyrametostrobin (915410-70-7) (WO 2004/058723), (3.19)pyraoxystrobin (862588-11-2) (WO 2004/058723), (3.20) pyribencarb(799247-52-2) (WO 2004/058723), (3.21) triclopyricarb (902760-40-1),(3.22) trifloxystrobin (141517-21-7) (WO 2004/058723), (3.23)(2E)-2-(2-{[6-(3-chloro-2-methylphenoxy)-5-fluoropyrimidin-4-yl]oxy}phenyl)-2-(methoxyimino)-N-methylethanamide(WO 2004/058723), (3.24)(2E)-2-(methoxyimino)-N-methyl-2-(2-{[({(1E)-1-[3-(trifluoromethyl)phenyl]ethylidene}amino)oxy]methyl}phenyl)ethanamide(WO 2004/058723), (3.25)(2E)-2-(methoxyimino)-N-methyl-2-{2-[(E)-({1-[3-(trifluoromethyl)phenyl]ethoxy}imino)methyl]phenyl}ethanamide(158169-73-4), (3.26)(2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenylethenyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylethanamide(326896-28-0), (3.27)(2E)-2-{2-[({[(2E,3E)-4-(2,6-dichlorophenyl)but-3-en-2-ylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylethanamide,(3.28)2-chloro-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)pyridine-3-carboxamide(119899-14-8), (3.29)5-methoxy-2-methyl-4-(2-{[({(1E)-1-[3-(trifluoromethyl)phenyl]ethylidene}amino)oxy]methyl}phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one,(3.30) methyl(2E)-2-{2-[({cyclopropyl[(4-methoxyphenyl)imino]methyl}sulfanyl)methyl]phenyl}-3-methoxprop-2-enoate(149601-03-6), (3.31)N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-(formylamino)-2-hydroxybenzamide(226551-21-9), (3.32)2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide(173662-97-0) and (3.33)(2R)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide(394657-24-0).(4) Inhibitors of the mitosis and cell division, for example (4.1)benomyl (17804-35-2), (4.2) carbendazim (10605-21-7), (4.3)chlorfenazole (3574-96-7), (4.4) diethofencarb (87130-20-9), (4.5)ethaboxam (162650-77-3), (4.6) fluopicolide (239110-15-7), (4.7)fuberidazole (3878-19-1), (4.8) pencycuron (66063-05-6), (4.9)thiabendazole (148-79-8), (4.10) thiophanate-methyl (23564-05-8), (4.11)thiophanate (23564-06-9), (4.12) zoxamide (156052-68-5), (4.13)5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidine(214706-53-3) and (4.14)3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine(1002756-87-7).(5) Compounds capable to have a multisite action, like for example (5.1)bordeaux mixture (8011-63-0), (5.2) captafol (2425-06-1), (5.3) captan(133-06-2) (WO 02/12172), (5.4) chlorothalonil (1897-45-6), (5.5) copperhydroxide (20427-59-2), (5.6) copper naphthenate (1338-02-9), (5.7)copper oxide (1317-39-1), (5.8) copper oxychloride (1332-40-7), (5.9)copper (2+) sulfate (7758-98-7), (5.10) dichlofluanid (1085-98-9),(5.11) dithianon (3347-22-6), (5.12) dodine (2439-10-3), (5.13) dodinefree base, (5.14) ferbam (14484-64-1), (5.15) fluorofolpet (719-96-0),(5.16) folpet (133-07-3), (5.17) guazatine (108173-90-6), (5.18)guazatine acetate, (5.19) iminoctadine (13516-27-3), (5.20) iminoctadinealbesilate (169202-06-6), (5.21) iminoctadine triacetate (57520-17-9),(5.22) mancopper (53988-93-5), (5.23) mancozeb (8018-01-7), (5.24) maneb(12427-38-2), (5.25) metiram (9006-42-2), (5.26) metiram zinc(9006-42-2), (5.27) oxine-copper (10380-28-6), (5.28) propamidine(104-32-5), (5.29) propineb (12071-83-9), (5.30) sulfur and sulfurpreparations including calcium polysulfide (7704-34-9), (5.31) thiram(137-26-8), (5.32) tolylfluanid (731-27-1), (5.33) zineb (12122-67-7)and (5.34) ziram (137-30-4).(6) Compounds capable to induce a host defence, for example (6.1)acibenzolar-5-methyl (135158-54-2), (6.2) isotianil (224049-04-1), (6.3)probenazole (27605-76-1) and (6.4) tiadinil (223580-51-6).(7) Inhibitors of the amino acid and/or protein biosynthesis, forexample (7.1) andoprim (23951-85-1), (7.2) blasticidin-S (2079-00-7),(7.3) cyprodinil (121552-61-2), (7.4) kasugamycin (6980-18-3), (7.5)kasugamycin hydrochloride hydrate (19408-46-9), (7.6) mepanipyrim(110235-47-7), (7.7) pyrimethanil (53112-28-0) and (7.8)3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinoline(861647-32-7) (WO2005070917).(8) Inhibitors of the ATP production, for example (8.1) fentin acetate(900-95-8), (8.2) fentin chloride (639-58-7), (8.3) fentin hydroxide(76-87-9) and (8.4) silthiofam (175217-20-6).(9) Inhibitors of the cell wall synthesis, for example (9.1)benthiavalicarb (177406-68-7), (9.2) dimethomorph (110488-70-5), (9.3)flumorph (211867-47-9), (9.4) iprovalicarb (140923-17-7), (9.5)mandipropamid (374726-62-2), (9.6) polyoxins (11113-80-7), (9.7)polyoxorim (22976-86-9), (9.8) validamycin A (37248-47-8) and (9.9)valifenalate (283159-94-4; 283159-90-0).(10) Inhibitors of the lipid and membrane synthesis, for example (10.1)biphenyl (92-52-4), (10.2) chloroneb (2675-77-6), (10.3) dicloran(99-30-9), (10.4) edifenphos (17109-49-8), (10.5) etridiazole(2593-15-9), (10.6) iodocarb (55406-53-6), (10.7) iprobenfos(26087-47-8), (10.8) isoprothiolane (50512-35-1), (10.9) propamocarb(25606-41-1), (10.10) propamocarb hydrochloride (25606-41-1), (10.11)prothiocarb (19622-08-3), (10.12) pyrazophos (13457-18-6), (10.13)quintozene (82-68-8), (10.14) tecnazene (117-18-0) and (10.15)tolclofos-methyl (57018-04-9).(11) Inhibitors of the melanine biosynthesis, for example (11.1)carpropamid (104030-54-8), (11.2) diclocymet (139920-32-4), (11.3)fenoxanil (115852-48-7), (11.4) phthalide (27355-22-2), (11.5)pyroquilon (57369-32-1), (11.6) tricyclazole (41814-78-2) and (11.7)2,2,2-trifluoroethyl{3-methyl-1-[(4-methylbenzoyl)amino]butan-2-yl}carbamate (851524-22-6)(WO2005042474).(12) Inhibitors of the nucleic acid synthesis, for example (12.1)benalaxyl (71626-11-4), (12.2) benalaxyl-M (kiralaxyl) (98243-83-5),(12.3) bupirimate (41483-43-6), (12.4) clozylacon (67932-85-8), (12.5)dimethirimol (5221-53-4), (12.6) ethirimol (23947-60-6), (12.7)furalaxyl (57646-30-7), (12.8) hymexazol (10004-44-1), (12.9) metalaxyl(57837-19-1), (12.10) metalaxyl-M (mefenoxam) (70630-17-0), (12.11)ofurace (58810-48-3), (12.12) oxadixyl (77732-09-3) and (12.13) oxolinicacid (14698-29-4).(13) Inhibitors of the signal transduction, for example (13.1)chlozolinate (84332-86-5), (13.2) fenpiclonil (74738-17-3), (13.3)fludioxonil (131341-86-1), (13.4) iprodione (36734-19-7), (13.5)procymidone (32809-16-8), (13.6) quinoxyfen (124495-18-7) and (13.7)vinclozolin (50471-44-8).(14) Compounds capable to act as an uncoupler, for example (14.1)binapacryl (485-31-4), (14.2) dinocap (131-72-6), (14.3) ferimzone(89269-64-7), (14.4) fluazinam (79622-59-6) and (14.5) meptyldinocap(131-72-6).(15) Further compounds, for example (15.1) benthiazole (21564-17-0),(15.2) bethoxazin (163269-30-5), (15.3) capsimycin (70694-08-5), (15.4)carvone (99-49-0), (15.5) chinomethionat (2439-01-2), (15.6) pyriofenone(chlazafenone) (688046-61-9), (15.7) cufraneb (11096-18-7), (15.8)cyflufenamid (180409-60-3), (15.9) cymoxanil (57966-95-7), (15.10)cyprosulfamide (221667-31-8), (15.11) dazomet (533-74-4), (15.12)debacarb (62732-91-6), (15.13) dichlorophen (97-23-4), (15.14)diclomezine (62865-36-5), (15.15) difenzoquat (49866-87-7), (15.16)difenzoquat methylsulfate (43222-48-6), (15.17) diphenylamine(122-39-4), (15.18) ecomate, (15.19) fenpyrazamine (473798-59-3),(15.20) flumetover (154025-04-4), (15.21) fluoroimide (41205-21-4),(15.22) flusulfamide (106917-52-6), (15.23) flutianil (304900-25-2),(15.24) fosetyl-aluminium (39148-24-8), (15.25) fosetyl-calcium, (15.26)fosetyl-sodium (39148-16-8), (15.27) hexachlorobenzene (118-74-1),(15.28) irumamycin (81604-73-1), (15.29) methasulfocarb (66952-49-6),(15.30) methyl isothiocyanate (556-61-6), (15.31) metrafenone(220899-03-6), (15.32) mildiomycin (67527-71-3), (15.33) natamycin(7681-93-8), (15.34) nickel dimethyldithiocarbamate (15521-65-0),(15.35) nitrothal-isopropyl (10552-74-6), (15.36) octhilinone(26530-20-1), (15.37) oxamocarb (917242-12-7), (15.38) oxyfenthiin(34407-87-9), (15.39) pentachlorophenol and salts (87-86-5), (15.40)phenothrin, (15.41) phosphorous acid and its salts (13598-36-2), (15.42)propamocarb-fosetylate, (15.43) propanosine-sodium (88498-02-6), (15.44)proquinazid (189278-12-4), (15.45) pyrimorph (868390-90-3), (15.45e)(2E)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one(1231776-28-5), (15.45z)(2Z)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one(1231776-29-6), (15.46) pyrrolnitrine (1018-71-9) (EP-A 1 559 320),(15.47) tebufloquin (376645-78-2), (15.48) tecloftalam (76280-91-6),(15.49) tolnifanide (304911-98-6), (15.50) triazoxide (72459-58-6),(15.51) trichlamide (70193-21-4), (15.52) zarilamid (84527-51-5),(15.53)(3S,6S,7R,8R)-8-benzyl-3-[({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl2-methylpropanoate (517875-34-2) (WO2003035617), (15.54)1-(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone(1003319-79-6) (WO 2008013622), (15.55)1-(4-{4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone(1003319-80-9) (WO 2008013622), (15.56)1-(4-{4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone(1003318-67-9) (WO 2008013622), (15.57)1-(4-methoxyphenoxy)-3,3-dimethylbutan-2-yl 1H-imidazole-1-carboxylate(111227-17-9), (15.58) 2,3,5,6-tetrachloro-4-(methylsulfonyl)pyridine(13108-52-6), (15.59)2,3-dibutyl-6-chlorothieno[2,3-d]pyrimidin-4(3H)-one (221451-58-7),(15.60)2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c′]dipyrrole-1,3,5,7(2H,6H)-tetrone,(15.61)2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(5R)-5-phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone(1003316-53-7) (WO 2008013622), (15.62)2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(5S)-5-phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone(1003316-54-8) (WO 2008013622), (15.63)2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-{4-[4-(5-phenyl-4,5-dihydro-1,2-oxazol-3-yl)-1,3-thiazol-2-yl]piperidin-1-yl}ethanone(1003316-51-5) (WO 2008013622), (15.64)2-butoxy-6-iodo-3-propyl-4H-chromen-4-one, (15.65)2-chloro-5-[2-chloro-1-(2,6-difluoro-4-methoxyphenyl)-4-methyl-1H-imidazol-5-yl]pyridine,(15.66) 2-phenylphenol and salts (90-43-7), (15.67)3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline(861647-85-0) (WO2005070917), (15.68)3,4,5-trichloropyridine-2,6-dicarbonitrile (17824-85-0), (15.69)3-[5-(4-chlorophenyl)-2,3-dimethyl-1,2-oxazolidin-3-yl]pyridine, (15.70)3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine,(15.71)4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpyridazine,(15.72) 5-amino-1,3,4-thiadiazole-2-thiol, (15.73)5-chloro-N′-phenyl-N′-(prop-2-yn-1-yl)thiophene-2-sulfonohydrazide(134-31-6), (15.74) 5-fluoro-2-[(4-fluorobenzyl)oxy]pyrimidin-4-amine(1174376-11-4) (WO2009094442), (15.75)5-fluoro-2-[(4-methylbenzyl)oxy]pyrimidin-4-amine (1174376-25-0)(WO2009094442), (15.76)5-methyl-6-octyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine, (15.77) ethyl(2Z)-3-amino-2-cyano-3-phenylprop-2-enoate, (15.78)N′-(4-{[3-(4-chlorobenzyl)-1,2,4-thiadiazol-5-yl]oxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide,(15.79)N-(4-chlorobenzyl)-3-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]propanamide,(15.80)N-[(4-chlorophenyl)(cyano)methyl]-3-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]propanamide,(15.81)N-[(5-bromo-3-chloropyridin-2-yl)methyl]-2,4-dichloropyridine-3-carboxamide,(15.82)N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2,4-dichloropyridine-3-carboxamide,(15.83)N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2-fluoro-4-iodopyridine-3-carboxamide,(15.84)N-{(E)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide(221201-92-9), (15.85)N-{(Z)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide(221201-92-9), (15.86)N′-{4-[(3-tert-butyl-4-cyano-1,2-thiazol-5-yl)oxy]-2-chloro-5-methylphenyl}-N-ethyl-N-methylimidoformamide,(15.87)N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-(1,2,3,4-tetrahydronaphthalen-1-yl)-1,3-thiazole-4-carboxamide(922514-49-6) (WO 2007014290), (15.88)N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazole-4-carboxamide(922514-07-6) (WO 2007014290), (15.89)N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-[(1S)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazole-4-carboxamide(922514-48-5) (WO 2007014290), (15.90) pentyl{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylidene]amino}oxy)methyl]pyridin-2-yl}carbamate,(15.91) phenazine-1-carboxylic acid, (15.92) quinolin-8-ol (134-31-6),(15.93) quinolin-8-ol sulfate (2:1) (134-31-6) and (15.94) tert-butyl{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate.(16) Further compounds, for example (16.1)1-methyl-3-(trifluoromethyl)-N-[2′-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide,(16.2)N-(4′-chlorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(16.3)N-(2′,4′-dichlorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(16.4)3-(difluoromethyl)-1-methyl-N-[4′-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide,(16.5)N-(2′,5′-difluorobiphenyl-2-yl)-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide,(16.6)3-(difluoromethyl)-1-methyl-N-[4′-(prop-1-yn-1-yl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide(known from WO 2004/058723), (16.7)5-fluoro-1,3-dimethyl-N-[4′-(prop-1-yn-1-yl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide(known from WO 2004/058723), (16.8)2-chloro-N-[4′-(prop-1-yn-1-yl)biphenyl-2-yl]pyridine-3-carboxamide(known from WO 2004/058723), (16.9)3-(difluoromethyl)-N-[4′-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]-1-methyl-1H-pyrazole-4-carboxamide(known from WO 2004/058723), (16.10)N-[4′-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide(known from WO 2004/058723), (16.11)3-(difluoromethyl)-N-(4′-ethynylbiphenyl-2-yl)-1-methyl-1H-pyrazole-4-carboxamide(known from WO 2004/058723), (16.12)N-(4′-ethynylbiphenyl-2-yl)-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide(known from WO 2004/058723), (16.13)2-chloro-N-(4′-ethynylbiphenyl-2-yl)pyridine-3-carboxamide (known fromWO 2004/058723), (16.14)2-chloro-N-[4′-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]pyridine-3-carboxamide(known from WO 2004/058723), (16.15)4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)biphenyl-2-yl]-1,3-thiazole-5-carboxamide(known from WO 2004/058723), (16.16)5-fluoro-N-[4′-(3-hydroxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1,3-dimethyl-1H-pyrazole-4-carboxamide(known from WO 2004/058723), (16.17)2-chloro-N-[4′-(3-hydroxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]pyridine-3-carboxamide(known from WO 2004/058723), (16.18)3-(difluoromethyl)-N-[4′-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1-methyl-1H-pyrazole-4-carboxamide(known from WO 2004/058723), (16.19)5-fluoro-N-[4′-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1,3-dimethyl-1H-pyrazole-4-carboxamide(known from WO 2004/058723), (16.20)2-chloro-N-[4′-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]pyridine-3-carboxamide(known from WO 2004/058723), (16.21)(5-bromo-2-methoxy-4-methylpyridin-3-yl)(2,3,4-trimethoxy-6-methylphenyl)methanone(known from EP-A 1 559 320), (16.22)N-[2-(4-{[3-(4-chlorophenyl)prop-2-yn-1-yl]oxy}-3-methoxyphenyl)ethyl]-N2-(methylsulfonyl)valinamide(220706-93-4), (16.23) 4-oxo-4-[(2-phenylethyl)amino]butanoic acid and(16.24) but-3-yn-1-yl{6-[({[(Z)-(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate.

All named mixing partners of the classes (1) to (16) can, if theirfunctional groups enable this, optionally form salts with suitable basesor acids.

The composition according to the invention comprising a mixture of acompound of formula (I) with a bactericide compound can also beparticularly advantageous. Examples of suitable bactericide mixingpartners can be selected in the following list: bronopol, dichlorophen,nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone,furancarboxylic acid, oxytetracycline, probenazole, streptomycin,tecloftalam, copper sulfate and other copper preparations.

The compounds of formula (I) and the fungicide composition according tothe invention can be used to curatively or preventively control thephytopathogenic fungi of plants or crops.

Thus, according to a further aspect of the invention, there is provideda method for curatively or preventively controlling the phytopathogenicfungi of plants or crops characterised in that a compound of formula (I)or a fungicide composition according to the invention is applied to theseed, the plant or to the fruit of the plant or to the soil wherein theplant is growing or wherein it is desired to grow.

The method of treatment according to the invention can also be useful totreat propagation material such as tubers or rhizomes, but also seeds,seedlings or seedlings pricking out and plants or plants pricking out.This method of treatment can also be useful to treat roots. The methodof treatment according to the invention can also be useful to treat theoverground parts of the plant such as trunks, stems or stalks, leaves,flowers and fruit of the concerned plant.

According to the invention all plants and plant parts can be treated. Byplants is meant all plants and plant populations such as desirable andundesirable wild plants, cultivars and plant varieties (whether or notprotectable by plant variety or plant breeder's rights). Cultivars andplant varieties can be plants obtained by conventional propagation andbreeding methods which can be assisted or supplemented by one or morebiotechnological methods such as by use of double haploids, protoplastfusion, random and directed mutagenesis, molecular or genetic markers orby bioengineering and genetic engineering methods. By plant parts ismeant all above ground and below ground parts and organs of plants suchas shoot, leaf, blossom and root, whereby for example leaves, needles,stems, branches, blossoms, fruiting bodies, fruits and seed as well asroots, corms and rhizomes are listed. Crops and vegetative andgenerative propagating material, for example cuttings, corms, rhizomes,runners and seeds also belong to plant parts.

Among the plants that can be protected by the method according to theinvention, mention may be made of major field crops like corn, soybean,cotton, Brassica oilseeds such as Brassica napus (e.g. canola), Brassicarapa, B. juncea (e.g. mustard) and Brassica carinata, rice, wheat,sugarbeet, sugarcane, oats, rye, barley, millet, triticale, flax, vineand various fruits and vegetables of various botanical taxa such asRosaceae sp. (for instance pip fruit such as apples and pears, but alsostone fruit such as apricots, cherries, almonds and peaches, berryfruits such as strawberries), Ribesioidae sp., Juglandaceae sp.,Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceaesp., Actimidaceae sp., Lauraceae sp., Musaceae sp. (for instance bananatrees and plantings), Rubiaceae sp. (for instance coffee), Theaceae sp.,Sterculiceae sp., Rutaceae sp. (for instance lemons, oranges andgrapefruit); Solanaceae sp. (for instance tomatoes, potatoes, peppers,eggplant), Liliaceae sp., Compositiae sp. (for instance lettuce,artichoke and chicory—including root chicory, endive or common chicory),Umbelliferae sp. (for instance carrot, parsley, celery and celeriac),Cucurbitaceae sp. (for instance cucumber—including pickling cucumber,squash, watermelon, gourds and melons), Alliaceae sp. (for instanceonions and leek), Cruciferae sp. (for instance white cabbage, redcabbage, broccoli, cauliflower, brussel sprouts, pak choi, kohlrabi,radish, horseradish, cress, Chinese cabbage), Leguminosae sp. (forinstance peanuts, peas and beans beans—such as climbing beans and broadbeans), Chenopodiaceae sp. (for instance mangold, spinach beet, spinach,beetroots), Malvaceae (for instance okra), Asparagaceae (for instanceasparagus); horticultural and forest crops; ornamental plants; as wellas genetically modified homologues of these crops.

The method of treatment according to the invention can be used in thetreatment of genetically modified organisms (GMOs), e.g. plants orseeds. Genetically modified plants (or transgenic plants) are plants ofwhich a heterologous gene has been stably integrated into genome. Theexpression “heterologous gene” essentially means a gene which isprovided or assembled outside the plant and when introduced in thenuclear, chloroplastic or mitochondrial genome gives the transformedplant new or improved agronomic or other properties by expressing aprotein or polypeptide of interest or by downregulating or silencingother gene(s) which are present in the plant (using for example,antisense technology, cosuppression technology or RNAinterference—RNAi—technology). A heterologous gene that is located inthe genome is also called a transgene. A transgene that is defined byits particular location in the plant genome is called a transformationor transgenic event.

Depending on the plant species or plant cultivars, their location andgrowth conditions (soils, climate, vegetation period, diet), thetreatment according to the invention may also result in additionaleffects. Thus, for example, reduced application rates and/or a wideningof the activity spectrum and/or an increase in the activity of theactive compounds and compositions which can be used according to theinvention, better plant growth, increased tolerance to high or lowtemperatures, increased tolerance to drought or to water or soil saltcontent, increased flowering performance, easier harvesting, acceleratedmaturation, higher harvest yields, bigger fruits, larger plant height,greener leaf color, earlier flowering, higher quality and/or a highernutritional value of the harvested products, higher sugar concentrationwithin the fruits, better storage stability and/or processability of theharvested products are possible, which exceed the effects which wereactually to be expected.

At certain application rates, the active compound combinations accordingto the invention may also have a strengthening effect in plants.Accordingly, they are also suitable for mobilizing the defense system ofthe plant against attack by unwanted microorganisms. This may, ifappropriate, be one of the reasons of the enhanced activity of thecombinations according to the invention, for example against fungi.Plant-strengthening (resistance-inducing) substances are to beunderstood as meaning, in the present context, those substances orcombinations of substances which are capable of stimulating the defensesystem of plants in such a way that, when subsequently inoculated withunwanted microorganisms, the treated plants display a substantial degreeof resistance to these microorganisms. In the present case, unwantedmicroorganisms are to be understood as meaning phytopathogenic fungi,bacteria and viruses. Thus, the substances according to the inventioncan be employed for protecting plants against attack by theabovementioned pathogens within a certain period of time after thetreatment. The period of time within which protection is effectedgenerally extends from 1 to 10 days, preferably 1 to 7 days, after thetreatment of the plants with the active compounds.

Plants and plant cultivars which are preferably to be treated accordingto the invention include all plants which have genetic material whichimpart particularly advantageous, useful traits to these plants (whetherobtained by breeding and/or biotechnological means).

Plants and plant cultivars which are also preferably to be treatedaccording to the invention are resistant against one or more bioticstresses, i.e. said plants show a better defense against animal andmicrobial pests, such as against nematodes, insects, mites,phytopathogenic fungi, bacteria, viruses and/or viroids.

Examples of nematode resistant plants are described in e.g. U.S. patentapplication Ser. Nos. 11/765,491, 11/765,494, 10/926,819, 10/782,020,12/032,479, 10/783,417, 10/782,096, 11/657,964, 12/192,904, 11/396,808,12/166,253, 12/166,239, 12/166,124, 12/166,209, 11/762,886, 12/364,335,11/763,947, 12/252,453, 12/209,354, 12/491,396 or 12/497,221.

Plants and plant cultivars which may also be treated according to theinvention are those plants which are resistant to one or more abioticstresses. Abiotic stress conditions may include, for example, drought,cold temperature exposure, heat exposure, osmotic stress, flooding,increased soil salinity, increased mineral exposure, ozone exposure,high light exposure, limited availability of nitrogen nutrients, limitedavailability of phosphorus nutrients, shade avoidance.

Plants and plant cultivars which may also be treated according to theinvention, are those plants characterized by enhanced yieldcharacteristics. Increased yield in said plants can be the result of,for example, improved plant physiology, growth and development, such aswater use efficiency, water retention efficiency, improved nitrogen use,enhanced carbon assimilation, improved photosynthesis, increasedgermination efficiency and accelerated maturation. Yield can furthermorebe affected by improved plant architecture (under stress and non-stressconditions), including but not limited to, early flowering, floweringcontrol for hybrid seed production, seedling vigor, plant size,internode number and distance, root growth, seed size, fruit size, podsize, pod or ear number, seed number per pod or ear, seed mass, enhancedseed filling, reduced seed dispersal, reduced pod dehiscence and lodgingresistance. Further yield traits include seed composition, such ascarbohydrate content, protein content, oil content and composition,nutritional value, reduction in anti-nutritional compounds, improvedprocessability and better storage stability.

Examples of plants with the above-mentioned traits are non-exhaustivelylisted in Table A.

Plants that may be treated according to the invention are hybrid plantsthat already express the characteristic of heterosis or hybrid vigorwhich results in generally higher yield, vigor, health and resistancetowards biotic and abiotic stresses). Such plants are typically made bycrossing an inbred male-sterile parent line (the female parent) withanother inbred male-fertile parent line (the male parent). Hybrid seedis typically harvested from the male sterile plants and sold to growers.Male sterile plants can sometimes (e.g. in corn) be produced bydetasseling, i.e. the mechanical removal of the male reproductive organs(or males flowers) but, more typically, male sterility is the result ofgenetic determinants in the plant genome. In that case, and especiallywhen seed is the desired product to be harvested from the hybrid plantsit is typically useful to ensure that male fertility in the hybridplants is fully restored. This can be accomplished by ensuring that themale parents have appropriate fertility restorer genes which are capableof restoring the male fertility in hybrid plants that contain thegenetic determinants responsible for male-sterility. Geneticdeterminants for male sterility may be located in the cytoplasm.Examples of cytoplasmic male sterility (CMS) were for instance describedin Brassica species (WO 92/05251, WO 95/09910, WO 98/27806, WO05/002324, WO 06/021972 and U.S. Pat. No. 6,229,072). However, geneticdeterminants for male sterility can also be located in the nucleargenome. Male sterile plants can also be obtained by plant biotechnologymethods such as genetic engineering. A particularly useful means ofobtaining male-sterile plants is described in WO 89/10396 in which, forexample, a ribonuclease such as barnase is selectively expressed in thetapetum cells in the stamens. Fertility can then be restored byexpression in the tapetum cells of a ribonuclease inhibitor such asbarstar (e.g. WO 91/02069).

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may be treated according to the inventionare herbicide-tolerant plants, i.e. plants made tolerant to one or moregiven herbicides. Such plants can be obtained either by genetictransformation, or by selection of plants containing a mutationimparting such herbicide tolerance.

Herbicide-resistant plants are for example glyphosate-tolerant plants,i.e. plants made tolerant to the herbicide glyphosate or salts thereof.Plants can be made tolerant to glyphosate through different means. Forexample, glyphosate-tolerant plants can be obtained by transforming theplant with a gene encoding the enzyme 5-enolpyruvylshikimate-3-phosphatesynthase (EPSPS). Examples of such EPSPS genes are the AroA gene (mutantCT7) of the bacterium Salmonella typhimurium (Comai et al., 1983,Science 221, 370-371), the CP4 gene of the bacterium Agrobacterium sp.(Barry et al., 1992, Curr. Topics Plant Physiol. 7, 139-145), the genesencoding a Petunia EPSPS (Shah et al., 1986, Science 233, 478-481), aTomato EPSPS (Gasser et al., 1988, J. Biol. Chem. 263, 4280-4289), or anEleusine EPSPS (WO 01/66704). It can also be a mutated EPSPS asdescribed in for example EP 0837944, WO 00/66746, WO 00/66747 orWO02/26995. Glyphosate-tolerant plants can also be obtained byexpressing a gene that encodes a glyphosate oxido-reductase enzyme asdescribed in U.S. Pat. Nos. 5,776,760 and 5,463,175. Glyphosate-tolerantplants can also be obtained by expressing a gene that encodes aglyphosate acetyl transferase enzyme as described in for example WO02/36782, WO 03/092360, WO 05/012515 and WO 07/024,782.Glyphosate-tolerant plants can also be obtained by selecting plantscontaining naturally-occurring mutations of the above-mentioned genes,as described in for example WO 01/024615 or WO 03/013226. Plantsexpressing EPSPS genes that confer glyphosate tolerance are described ine.g. U.S. patent application Ser. Nos. 11/517,991, 10/739,610,12/139,408, 12/352,532, 11/312,866, 11/315,678, 12/421,292, 11/400,598,11/651,752, 11/681,285, 11/605,824, 12/468,205, 11/760,570, 11/762,526,11/769,327, 11/769,255, 11/943,801 or 12/362,774. Plants comprisingother genes that confer glyphosate tolerance, such as decarboxylasegenes, are described in e.g. U.S. patent application Ser. Nos.11/588,811, 11/185,342, 12/364,724, 11/185,560 or 12/423,926.

Other herbicide resistant plants are for example plants that are madetolerant to herbicides inhibiting the enzyme glutamine synthase, such asbialaphos, phosphinothricin or glufosinate. Such plants can be obtainedby expressing an enzyme detoxifying the herbicide or a mutant glutaminesynthase enzyme that is resistant to inhibition, e.g. described in U.S.patent application Ser. No. 11/760,602. One such efficient detoxifyingenzyme is an enzyme encoding a phosphinothricin acetyltransferase (suchas the bar or pat protein from Streptomyces species). Plants expressingan exogenous phosphinothricin acetyltransferase are for exampledescribed in U.S. Pat. Nos. 5,561,236; 5,648,477; 5,646,024; 5,273,894;5,637,489; 5,276,268; 5,739,082; 5,908,810 and 7,112,665.

Further herbicide-tolerant plants are also plants that are made tolerantto the herbicides inhibiting the enzyme hydroxphenylpyruvatedioxygenase(HPPD). Hydroxphenylpyruvatedioxnenases are enzymes that catalyze thereaction in which para-hydroxyphenylpyruvate (HPP) is transformed intohomogentisate. Plants tolerant to HPPD-inhibitors can be transformedwith a gene encoding a naturally-occurring resistant HPPD enzyme, or agene encoding a mutated or chimeric HPPD enzyme as described in WO96/38567, WO 99/24585, WO 99/24586, WO 2009/144079, WO 2002/046387, orU.S. Pat. No. 6,768,044. Tolerance to HPPD-inhibitors can also beobtained by transforming plants with genes encoding certain enzymesenabling the formation of homogentisate despite the inhibition of thenative HPPD enzyme by the HPPD-inhibitor. Such plants and genes aredescribed in WO 99/34008 and WO 02/36787. Tolerance of plants to HPPDinhibitors can also be improved by transforming plants with a geneencoding an enzyme having prephenate deshydrogenase (PDH) activity inaddition to a gene encoding an HPPD-tolerant enzyme, as described in WO2004/024928. Further, plants can be made more tolerant to HPPD-inhibitorherbicides by adding into their genome a gene encoding an enzyme capableof metabolizing or degrading HPPD inhibitors, such as the CYP450 enzymesshown in WO 2007/103567 and WO 2008/150473.

Still further herbicide resistant plants are plants that are madetolerant to acetolactate synthase (ALS) inhibitors. Known ALS-inhibitorsinclude, for example, sulfonylurea, imidazolinone, triazolopyrimidines,pryimidinyoxy(thio)benzoates, and/or sulfonylaminocarbonyltriazolinoneherbicides. Different mutations in the ALS enzyme (also known asacetohydroxyacid synthase, AHAS) are known to confer tolerance todifferent herbicides and groups of herbicides, as described for examplein Tranel and Wright (2002, Weed Science 50:700-712), but also, in U.S.Pat. Nos. 5,605,011, 5,378,824, 5,141,870, and 5,013,659. The productionof sulfonylurea-tolerant plants and imidazolinone-tolerant plants isdescribed in U.S. Pat. Nos. 5,605,011; 5,013,659; 5,141,870; 5,767,361;5,731,180; 5,304,732; 4,761,373; 5,331,107; 5,928,937; and 5,378,824;and international publication WO 96/33270. Other imidazolinone-tolerantplants are also described in for example WO 2004/040012, WO 2004/106529,WO 2005/020673, WO 2005/093093, WO 2006/007373, WO 2006/015376, WO2006/024351, and WO 2006/060634. Further sulfonylurea- andimidazolinone-tolerant plants are also described in for example WO07/024,782 and U.S. Patent Application No. 61/288,958.

Other plants tolerant to imidazolinone and/or sulfonylurea can beobtained by induced mutagenesis, selection in cell cultures in thepresence of the herbicide or mutation breeding as described for examplefor soybeans in U.S. Pat. No. 5,084,082, for rice in WO 97/41218, forsugar beet in U.S. Pat. No. 5,773,702 and WO 99/057965, for lettuce inU.S. Pat. No. 5,198,599, or for sunflower in WO 01/065922.

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may also be treated according to theinvention are insect-resistant transgenic plants, i.e. plants maderesistant to attack by certain target insects. Such plants can beobtained by genetic transformation, or by selection of plants containinga mutation imparting such insect resistance.

An “insect-resistant transgenic plant”, as used herein, includes anyplant containing at least one transgene comprising a coding sequenceencoding:

-   -   1) an insecticidal crystal protein from Bacillus thuringiensis        or an insecticidal portion thereof, such as the insecticidal        crystal proteins listed by Crickmore et al. (1998, Microbiology        and Molecular Biology Reviews, 62: 807-813), updated by        Crickmore et al. (2005) at the Bacillus thuringiensis toxin        nomenclature, online at:        http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/), or        insecticidal portions thereof, e.g., proteins of the Cry protein        classes Cry1Ab, Cry1Ac, Cry1B, Cry1C, Cry1D, Cry1F, Cry2Ab,        Cry3Aa, or Cry3Bb or insecticidal portions thereof (e.g. EP        1999141 and WO 2007/107302), or such proteins encoded by        synthetic genes as e.g. described in and U.S. patent application        Ser. No. 12/249,016; or    -   2) a crystal protein from Bacillus thuringiensis or a portion        thereof which is insecticidal in the presence of a second other        crystal protein from Bacillus thuringiensis or a portion        thereof, such as the binary toxin made up of the Cry34 and Cry35        crystal proteins (Moellenbeck et al. 2001, Nat. Biotechnol. 19:        668-72; Schnepf et al. 2006, Applied Environm. Microbiol. 71,        1765-1774) or the binary toxin made up of the Cry1A or Cry1F        proteins and the Cry2Aa or Cry2Ab or Cry2Ae proteins (U.S.        patent application Ser. No. 12/214,022 and EP 08010791.5); or    -   3) a hybrid insecticidal protein comprising parts of different        insecticidal crystal proteins from Bacillus thuringiensis, such        as a hybrid of the proteins of 1) above or a hybrid of the        proteins of 2) above, e.g., the Cry1A. 105 protein produced by        corn event MON89034 (WO 2007/027777); or 4) a protein of any one        of 1) to 3) above wherein some, particularly 1 to 10, amino        acids have been replaced by another amino acid to obtain a        higher insecticidal activity to a target insect species, and/or        to expand the range of target insect species affected, and/or        because of changes introduced into the encoding DNA during        cloning or transformation, such as the Cry3Bb1 protein in corn        events MON863 or MON88017, or the Cry3A protein in corn event        MIR604; or    -   5) an insecticidal secreted protein from Bacillus thuringiensis        or Bacillus cereus, or an insecticidal portion thereof, such as        the vegetative insecticidal (VIP) proteins listed at:        http://www.lifesci.sussex.ac.uk/home/Neil_Crickmore/Bt/vip.html,        e.g., proteins from the VIP3Aa protein class; or    -   6) a secreted protein from Bacillus thuringiensis or Bacillus        cereus which is insecticidal in the presence of a second        secreted protein from Bacillus thuringiensis or B. cereus, such        as the binary toxin made up of the VIP1A and VIP2A proteins (WO        94/21795); or    -   7) a hybrid insecticidal protein comprising parts from different        secreted proteins from Bacillus thuringiensis or Bacillus        cereus, such as a hybrid of the proteins in 1) above or a hybrid        of the proteins in 2) above; or    -   8) a protein of any one of 5) to 7) above wherein some,        particularly 1 to 10, amino acids have been replaced by another        amino acid to obtain a higher insecticidal activity to a target        insect species, and/or to expand the range of target insect        species affected, and/or because of changes introduced into the        encoding DNA during cloning or transformation (while still        encoding an insecticidal protein), such as the VIP3Aa protein in        cotton event COT102; or    -   9) a secreted protein from Bacillus thuringiensis or Bacillus        cereus which is insecticidal in the presence of a crystal        protein from Bacillus thuringiensis, such as the binary toxin        made up of VIP3 and Cry1A or Cry1F (U.S. Patent Appl. No.        61/126,083 and 61/195,019), or the binary toxin made up of the        VIP3 protein and the Cry2Aa or Cry2Ab or Cry2Ae proteins (U.S.        patent application Ser. No. 12/214,022 and EP 08010791.5).    -   10) a protein of 9) above wherein some, particularly 1 to 10,        amino acids have been replaced by another amino acid to obtain a        higher insecticidal activity to a target insect species, and/or        to expand the range of target insect species affected, and/or        because of changes introduced into the encoding DNA during        cloning or transformation (while still encoding an insecticidal        protein)

Of course, an insect-resistant transgenic plant, as used herein, alsoincludes any plant comprising a combination of genes encoding theproteins of any one of the above classes 1 to 10. In one embodiment, aninsect-resistant plant contains more than one transgene encoding aprotein of any one of the above classes 1 to 10, to expand the range oftarget insect species affected when using different proteins directed atdifferent target insect species, or to delay insect resistancedevelopment to the plants by using different proteins insecticidal tothe same target insect species but having a different mode of action,such as binding to different receptor binding sites in the insect.

An “insect-resistant transgenic plant”, as used herein, further includesany plant containing at least one transgene comprising a sequenceproducing upon expression a double-stranded RNA which upon ingestion bya plant insect pest inhibits the growth of this insect pest, asdescribed e.g. in WO 2007/080126, WO 2006/129204, WO 2007/074405, WO2007/080127 and WO 2007/035650.

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may also be treated according to theinvention are tolerant to abiotic stresses. Such plants can be obtainedby genetic transformation, or by selection of plants containing amutation imparting such stress resistance. Particularly useful stresstolerance plants include:

-   -   1) plants which contain a transgene capable of reducing the        expression and/or the activity of poly(ADP-ribose) polymerase        (PARP) gene in the plant cells or plants as described in WO        00/04173, WO/2006/045633, EP 04077984.5, or EP 06009836.5.    -   2) plants which contain a stress tolerance enhancing transgene        capable of reducing the expression and/or the activity of the        PARG encoding genes of the plants or plants cells, as described        e.g. in WO 2004/090140.    -   3) plants which contain a stress tolerance enhancing transgene        coding for a plant-functional enzyme of the nicotineamide        adenine dinucleotide salvage synthesis pathway including        nicotinamidase, nicotinate phosphoribosyltransferase, nicotinic        acid mononucleotide adenyl transferase, nicotinamide adenine        dinucleotide synthetase or nicotine amide        phosphorybosyltransferase as described e.g. in EP 04077624.7, WO        2006/133827, PCT/EP07/002,433, EP 1999263, or WO 2007/107326.

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may also be treated according to theinvention show altered quantity, quality and/or storage-stability of theharvested product and/or altered properties of specific ingredients ofthe harvested product such as:

-   -   1) transgenic plants which synthesize a modified starch, which        in its physical-chemical characteristics, in particular the        amylose content or the amylose/amylopectin ratio, the degree of        branching, the average chain length, the side chain        distribution, the viscosity behaviour, the gelling strength, the        starch grain size and/or the starch grain morphology, is changed        in comparison with the synthesised starch in wild type plant        cells or plants, so that this is better suited for special        applications. Said transgenic plants synthesizing a modified        starch are disclosed, for example, in EP 0571427, WO 95/04826,        EP 0719338, WO 96/15248, WO 96/19581, WO 96/27674, WO 97/11188,        WO 97/26362, WO 97/32985, WO 97/42328, WO 97/44472, WO 97/45545,        WO 98/27212, WO 98/40503, WO99/58688, WO 99/58690, WO 99/58654,        WO 00/08184, WO 00/08185, WO 00/08175, WO 00/28052, WO 00/77229,        WO 01/12782, WO 01/12826, WO 02/101059, WO 03/071860, WO        2004/056999, WO 2005/030942, WO 2005/030941, WO 2005/095632, WO        2005/095617, WO 2005/095619, WO 2005/095618, WO 2005/123927, WO        2006/018319, WO 2006/103107, WO 2006/108702, WO 2007/009823, WO        00/22140, WO 2006/063862, WO 2006/072603, WO 02/034923, EP        06090134.5, EP 06090228.5, EP 06090227.7, EP 07090007.1, EP        07090009.7, WO 01/14569, WO 02/79410, WO 03/33540, WO        2004/078983, WO 01/19975, WO 95/26407, WO 96/34968, WO 98/20145,        WO 99/12950, WO 99/66050, WO 99/53072, U.S. Pat. No. 6,734,341,        WO 00/11192, WO 98/22604, WO 98/32326, WO 01/98509, WO 01/98509,        WO 2005/002359, U.S. Pat. No. 5,824,790, U.S. Pat. No.        6,013,861, WO 94/04693, WO 94/09144, WO 94/11520, WO 95/35026,        WO 97/20936    -   2) transgenic plants which synthesize non starch carbohydrate        polymers or which synthesize non starch carbohydrate polymers        with altered properties in comparison to wild type plants        without genetic modification. Examples are plants producing        polyfructose, especially of the inulin and levan-type, as        disclosed in EP 0663956, WO 96/01904, WO 96/21023, WO 98/39460,        and WO 99/24593, plants producing alpha-1,4-glucans as disclosed        in WO 95/31553, US 2002031826, U.S. Pat. No. 6,284,479, U.S.        Pat. No. 5,712,107, WO 97/47806, WO 97/47807, WO 97/47808 and WO        00/14249, plants producing alpha-1,6 branched alpha-1,4-glucans,        as disclosed in WO 00/73422, plants producing alternan, as        disclosed in e.g. WO 00/47727, WO 00/73422, EP 06077301.7, U.S.        Pat. No. 5,908,975 and EP 0728213,    -   3) transgenic plants which produce hyaluronan, as for example        disclosed in WO 2006/032538, WO 2007/039314, WO 2007/039315, WO        2007/039316, JP 2006304779, and WO 2005/012529.    -   4) transgenic plants or hybrid plants, such as onions with        characteristics such as ‘high soluble solids content’, ‘low        pungency’ (LP) and/or ‘long storage’ (LS), as described in U.S.        patent application Ser. No. 12/020,360 and 61/054,026.

Plants or plant cultivars (that can be obtained by plant biotechnologymethods such as genetic engineering) which may also be treated accordingto the invention are plants, such as cotton plants, with altered fibercharacteristics. Such plants can be obtained by genetic transformation,or by selection of plants contain a mutation imparting such alteredfiber characteristics and include:

-   -   a) Plants, such as cotton plants, containing an altered form of        cellulose synthase genes as described in WO 98/00549    -   b) Plants, such as cotton plants, containing an altered form of        rsw2 or rsw3 homologous nucleic acids as described in WO        2004/053219    -   c) Plants, such as cotton plants, with increased expression of        sucrose phosphate synthase as described in WO 01/17333    -   d) Plants, such as cotton plants, with increased expression of        sucrose synthase as described in WO 02/45485    -   e) Plants, such as cotton plants, wherein the timing of the        plasmodesmatal gating at the basis of the fiber cell is altered,        e.g. through downregulation of fiber-selective β-1,3-glucanase        as described in WO 2005/017157, or as described in EP 08075514.3        or U.S. Patent Appl. No. 61/128,938    -   f) Plants, such as cotton plants, having fibers with altered        reactivity, e.g. through the expression of        N-acetylglucosaminetransferase gene including nodC and chitin        synthase genes as described in WO 2006/136351

Plants or plant cultivars (that can be obtained by plant biotechnologymethods such as genetic engineering) which may also be treated accordingto the invention are plants, such as oilseed rape or related Brassicaplants, with altered oil profile characteristics. Such plants can beobtained by genetic transformation, or by selection of plants contain amutation imparting such altered oil profile characteristics and include:

-   -   a) Plants, such as oilseed rape plants, producing oil having a        high oleic acid content as described e.g. in U.S. Pat. No.        5,969,169, U.S. Pat. No. 5,840,946 or U.S. Pat. No. 6,323,392 or        U.S. Pat. No. 6,063,947    -   b) Plants such as oilseed rape plants, producing oil having a        low linolenic acid content as described in U.S. Pat. No.        6,270,828, U.S. Pat. No. 6,169,190, or U.S. Pat. No. 5,965,755    -   c) Plant such as oilseed rape plants, producing oil having a low        level of saturated fatty acids as described e.g. in U.S. Pat.        No. 5,434,283 or U.S. patent application Ser. No. 12/668,303

Plants or plant cultivars (that can be obtained by plant biotechnologymethods such as genetic engineering) which may also be treated accordingto the invention are plants, such as oilseed rape or related Brassicaplants, with altered seed shattering characteristics. Such plants can beobtained by genetic transformation, or by selection of plants contain amutation imparting such altered seed shattering characteristics andinclude plants such as oilseed rape plants with delayed or reduced seedshattering as described in U.S. Patent Appl. No. 61/135,230 WO09/068,313and WO10/006,732.

Particularly useful transgenic plants which may be treated according tothe invention are plants containing transformation events, orcombination of transformation events, that are the subject of petitionsfor non-regulated status, in the United States of America, to the Animaland Plant Health Inspection Service (APHIS) of the United StatesDepartment of Agriculture (USDA) whether such petitions are granted orare still pending. At any time this information is readily availablefrom APHIS (4700 River Road Riverdale, Md. 20737, USA), for instance onits internet site (URL http://www.aphis.usda.gov/brs/not_reg.html). Onthe filing date of this application the petitions for nonregulatedstatus that were pending with APHIS or granted by APHIS were thoselisted in table B which contains the following information:

-   -   Petition: the identification number of the petition. Technical        descriptions of the transformation events can be found in the        individual petition documents which are obtainable from APHIS,        for example on the APHIS website, by reference to this petition        number. These descriptions are herein incorporated by reference.    -   Extension of Petition: reference to a previous petition for        which an extension is requested.    -   Institution: the name of the entity submitting the petition.    -   Regulated article: the plant species concerned.    -   Transgenic phenotype: the trait conferred to the plants by the        transformation event.    -   Transformation event or line: the name of the event or events        (sometimes also designated as lines or lines) for which        nonregulated status is requested.    -   APHIS documents: various documents published by APHIS in        relation to the Petition and which can be requested with APHIS.

Additional particularly useful plants containing single transformationevents or combinations of transformation events are listed for examplein the databases from various national or regional regulatory agencies(see for example http://gmoinfo.jrc.it/gmp_browse.aspx andhttp://www.agbios.com/dbase.php).

Further particularly transgenic plants include plants containing atransgene in an agronomically neutral or beneficial position asdescribed in any of the patent publications listed in Table C.

TABLE A Trait Reference Water use efficiency WO 2000/073475 Nitrogen useefficiency WO 1995/009911 WO 2007/076115 WO 1997/030163 WO 2005/103270WO 2007/092704 WO 2002/002776 Improved photosynthesis WO 2008/056915 WO2004/101751 Nematode resistance WO 1995/020669 WO 2003/033651 WO2001/051627 WO 1999/060141 WO 2008/139334 WO 1998/012335 WO 2008/095972WO 1996/030517 WO 2006/085966 WO 1993/018170 Reduced pod dehiscence WO2006/009649 WO 1997/013865 WO 2004/113542 WO 1996/030529 WO 1999/015680WO 1994/023043 WO 1999/000502 Aphid resistance WO 2006/125065 WO2008/067043 WO 1997/046080 WO 2004/072109 Sclerotinia resistance WO2006/135717 WO 2005/000007 WO 2006/055851 WO 2002/099385 WO 2005/090578WO 2002/061043 Botrytis resistance WO 2006/046861 WO 2002/085105 Bremiaresistance US 20070022496 WO 2004/049786 WO 2000/063432 Erwiniaresistance WO 2004/049786 Closterovirus resistance WO 2007/073167 WO2002/022836 WO 2007/053015 Stress tolerance (including WO 2010/019838 WO2008/002480 drought tolerance) WO 2009/049110 WO 2005/033318 Tobamovirusresistance WO 2006/038794

TABLE B Petitions of Nonregulated Status Granted or Pending by APHIS asof Mar. 31, 2010 Applicant Document Extension of Petition RegulatedTransgenic Transformation Petition Number *** Institution ArticlePhenotype Event or Line Petitions for Nonregulated Status Pending10-070-01p Virginia Tech Peanut Sclerotinia blight resistant N70, P39,and W171 09-349-01p Dow AgroSciences Soybean Herbicide TolerantDAS-68416-4 09-328-01p Bayer Crop Science Soybean Herbicide TolerantFG72 09-233-01p Dow Corn Herbicide Tolerant DAS-40278-9 09-201-01pMonsanto Soybean MON-877Ø5-6 09-183-01p Monsanto Soybean MON-8776909-082-01p Monsanto Soybean Lepidopteran resistant MON 87701 09-063-01pStine Seed Corn Glyphosate tolerant HCEM485 09-055-01p Monsanto CornDrought Tolerant MON 87460 09-015-01p BASF Plant Soybean HerbicideTolerant BPS-CV127-9 Science, LLC Soybean 08-366-01p ArborGen EucalyptusFreeze Tolerant, ARB-FTE1-08 Fertility Altered 08-340-01p Bayer CottonGlufosinate Tolerant, T304-40XGHB119 Insect Resistant 08-338-01p PioneerCorn Male Sterile, Fertility DP-32138-1 Restored, Visual Marker08-315-01p Florigene Rose Altered Flower Color IFD-524Ø1-4 andIFD-529Ø1-9 07-253-01p Syngenta Corn Lepidopteran resistant MIR-162Maize 07-108-01p Syngenta Cotton Lepidopteran Resistant COT67B06-354-01p Pioneer Soybean High Oleic Acid DP-3Ø5423-1 05-280-01pSyngenta Corn Thermostable alpha- 3272 amylase 04-110-01p Monsanto &Alfalfa Glyphosate Tolerant J101, J163 Forage Genetics 03-104-01pMonsanto & Creeping Glyphosate Tolerant ASR368 Scotts bentgrassPetitions for Nonregulated Status Granted 07-152-01p Pioneer Cornglyphosate & DP-098140-6 Imidazolinone tolerant 04-337-01p University ofPapaya Papaya Ringspot Virus X17-2 Florida Resistant 06-332-01p BayerCropScience Cotton Glyphosate tolerant GHB614 06-298-01p Monsanto CornEuropean Corn Borer MON 89034 resistant 06-271-01p Pioneer SoybeanGlyphosate & acetolactate 356043 synthase tolerant (DP-356Ø43-5)06-234-01p 98-329-01p Bayer CropScience Rice Phosphinothricin tolerantLLRICE601 06-178-01p Monsanto Soybean Glyphosate tolerant MON 8978804-362-01p Syngenta Corn Corn Rootworm Protected MIR604 04-264-01p ARSPlum Plum Pox Virus Resistant C5 04-229-01p Monsanto Corn High LysineLY038 04-125-01p Monsanto Corn Corn Rootworm Resistant 88017 04-086-01pMonsanto Cotton Glyphosate Tolerant MON 88913 03-353-01p Dow Corn CornRootworm Resistant 59122 03-323-01p Monsanto Sugar Beet GlyphosateTolerant H7-1 03-181-01p 00-136-01p Dow Corn Lepidopteran Resistant &TC-6275 Phosphinothricin tolerant 03-155-01p Syngenta CottonLepidopteran Resistant COT 102 03-036-01p Mycogen/Dow CottonLepidopteran Resistant 281-24-236 03-036-02p Mycogen/Dow CottonLepidopteran Resistant 3006-210-23 02-042-01p Aventis CottonPhosphinothericin tolerant LLCotton25 01-324-01p 98-216-01p MonsantoRapeseed Glyphosate tolerant RT200 01-206-01p 98-278-01p AventisRapeseed Phosphinothricin tolerant & MS1 & RF1/RF2 pollination control01-206-02p 97-205-01p Aventis Rapeseed Phosphinothricin tolerant Topas19/2 01-137-01p Monsanto Corn Corn Rootworm Resistant MON 863 01-121-01pVector Tobacco Reduced nicotine Vector 21-41 00-342-01p Monsanto CottonLepidopteran resistant Cotton Event 15985 00-136-01p Mycogen c/o CornLepidopteran resistant Line 1507 Dow & Pioneer phosphinothricin tolerant00-011-01p 97-099-01p Monsanto Corn Glyphosate tolerant NK603 99-173-01p97-204-01p Monsanto Potato PLRV & CPB resistant RBMT22-82 98-349-01p95-228-01p AgrEvo Corn Phosphinothricin MS6 tolerant and Male sterile98-335-01p U. of Flax Tolerant to soil CDC Triffid Saskatchewan residuesof sulfonyl urea herbicide 98-329-01p AgrEvo Rice Phosphinothricintolerant LLRICE06, LLRICE62 98-278-01p AgrEvo Rapeseed Phosphinothricintolerant & MS8 & RF3 Pollination control 98-238-01p AgrEvo SoybeanPhosphinothricin tolerant GU262 98-216-01p Monsanto Rapeseed Glyphosatetolerant RT73 98-173-01p Novartis Seeds & Beet Glyphosate tolerantGTSB77 Monsanto 98-014-01p 96-068-01p AgrEvo Soybean Phosphinothricintolerant A5547-127 97-342-01p Pioneer Corn Male sterile & 676, 678, 680Phosphinothricin tolerant 97-339-01p Monsanto Potato CPB & PVY resistantRBMT15-101, SEMT15-02, SEMT 15-15 97-336-01p AgrEvo BeetPhosphinothricin tolerant T-120-7 97-287-01p Monsanto TomatoLepidopteran resistant 5345 97-265-01p AgrEvo Corn PhosphinothricinCBH-351 tolerant & Lep. resistant 97-205-01p AgrEvo RapeseedPhosphinothricin tolerant T45 97-204-01p Monsanto Potato CPB & PLRVresistant RBMT21-129 & RBMT21-350 97-148-01p Bejo Cichorium Male sterileRM3-3, RM3-4, intybus RM3-6 97-099-01p Monsanto Corn Glyphosate tolerantGA21 97-013-01p Calgene Cotton Bromoxynil tolerant & Events 31807 &Lepidopteran resistant 31808 97-008-01p Du Pont Soybean Oil profilealtered G94-1, G94-19, G-168 96-317-01p Monsanto Corn Glyphosatetolerant & MON802 ECB resistant 96-291-01p DeKalb Corn European CornBorer DBT418 resistant 96-248-01p 92-196-01p Calgene Tomato Fruitripening altered 1 additional FLAVRSAVR line 96-068-01p AgrEvo SoybeanPhosphinothricin W62, W98, A2704- tolerant 12, A2704-21, A5547-3596-051-01p Cornell U Papaya PRSV resistant 55-1, 63-1 96-017-01p95-093-01p Monsanto Corn European Corn Borer MON809 & MON810 resistant95-352-01p Asgrow Squash CMV, ZYMV, WMV2 CZW-3 resistant 95-338-01pMonsanto Potato CPB resistant SBT02-5 & -7, ATBT04-6 & -27, -30, -31,-36 95-324-01p Agritope Tomato Fruit ripening altered 35 1 N 95-256-01pDu Pont Cotton Sulfonylurea tolerant 19-51a 95-228-01p Plant GeneticCorn Male sterile MS3 Systems 95-195-01p Northrup King Corn EuropeanCorn Borer Bt11 resistant 95-179-01p 92-196-01p Calgene Tomato Fruitripening altered 2 additional FLAVRSAVR lines 95-145-01p DeKalb CornPhosphinothricin tolerant B16 95-093-01p Monsanto Corn Lepidopteranresistant MON 80100 95-053-01p Monsanto Tomato Fruit ripening altered8338 95-045-01p Monsanto Cotton Glyphosate tolerant 1445, 169895-030-01p 92-196-01p Calgene Tomato Fruit ripening altered 20additional FLAVRSAVR lines 94-357-01p AgrEvo Corn Phosphinothricintolerant T14, T25 94-319-01p Ciba Seeds Corn Lepidopteran resistantEvent 176 94-308-01p Monsanto Cotton Lepidopteran resistant 531, 757,1076 94-290-01p Zeneca & Tomato Fruit polygalacturonase B, Da, FPetoseed level decreased 94-257-01p Monsanto Potato Coleopteranresistant BT6, BT10, BT12, BT16, BT17, BT18, BT23 94-230-01p 92-196-01pCalgene Tomato Fruit ripening altered 9 additional FLAVRSAVR lines94-228-01p DNA Plant Tech Tomato Fruit ripening altered 1345-494-227-01p 92-196-01p Calgene Tomato Fruit ripening altered Line N731436-111 94-090-01p Calgene Rapeseed Oil profile alteredpCGN3828-212/86-18 & 23 93-258-01p Monsanto Soybean Glyphosate tolerant40-3-2 93-196-01p Calgene Cotton Bromoxynil tolerant BXN 92-204-01pUpjohn Squash WMV2 & ZYMV ZW-20 resistant 92-196-01p Calgene TomatoFruit ripening altered FLAVR SAVR NOTE: To obtain the most up-to-datelist of Crops No Longer Regulated, please look at the Current Status ofPetitions. This list is automatically updated and reflects all petitionsreceived to date by APHIS, including petitions pending, withdrawn, orapproved. Abbreviations: CMV—cucumber mosaic virus; CPB—colorado potatobeetle; PLRV—potato leafroll virus; PRSV—papaya ringspot virus;PVY—potato virus Y; WMV2—watermelon mosaic virus 2 ZYMV—zucchini yellowmosaic virus *** Extension of Petition Number: Under 7CFR 340.6(e) aperson may request that APHIS extend a determination of non-regulatedstatus to other organisms based on their similarity of the previouslyderegulated article. This column lists the previously granted petitionof that degregulated article. **** Preliminary EA: The EnvironmentalAssessment initially available for Public comment prior to finalization.

TABLE C Plant species Event Trait Patent reference Corn PV-ZMGT32(NK603) Glyphosate tolerance US 2007-056056 Corn MIR604 Insectresistance (Cry3a055) EP 1 737 290 Corn LY038 High lysine content U.S.Pat. No. 7,157,281 Corn 3272 Self processing corn (alpha- US 2006-230473amylase) Corn PV-ZMIR13 Insect resistance (Cry3Bb) US 2006-095986(MON863) Corn DAS-59122-7 Insect resistance US 2006-070139(Cry34Ab1/Cry35Ab1) Corn TC1507 Insect resistance (Cry1F) U.S. Pat. No.7,435,807 Corn MON810 Insect resistance (Cry1Ab) US 2004-180373 CornVIP1034 Insect resistance WO 03/052073 Corn B16 Glufosinate resistanceUS 2003-126634 Corn GA21 Glyphosate resistance U.S. Pat. No. 6,040,497Corn GG25 Glyphosate resistance U.S. Pat. No. 6,040,497 Corn GJ11Glyphosate resistance U.S. Pat. No. 6,040,497 Corn FI117 Glyphosateresistance U.S. Pat. No. 6,040,497 Corn GAT-ZM1 Glufosinate tolerance WO01/51654 Corn MON87460 Drought tolerance WO 2009/111263 Corn DP-098140-6Glyphosate tolerance/ALS WO 2008/112019 inhibitor tolerance Wheat Event1 Fusarium resistance CA 2561992 (trichothecene 3-O- acetyltransferase)Sugar beet T227-1 Glyphosate tolerance US 2004-117870 Sugar beet H7-1Glyphosate tolerance WO 2004-074492 Soybean MON89788 Glyphosatetolerance US 2006-282915 Soybean A2704-12 Glufosinate tolerance WO2006/108674 Soybean A5547-35 Glufosinate tolerance WO 2006/108675Soybean DP-305423-1 High oleic acid/ALS inhibitor WO 2008/054747tolerance Rice GAT-OS2 Glufosinate tolerance WO 01/83818 Rice GAT-OS3Glufosinate tolerance US 2008-289060 Rice PE-7 Insect resistance(Cry1Ac) WO 2008/114282 Oilseed rape MS-B2 Male sterility WO 01/31042Oilseed rape MS-BN1/RF-BN1 Male sterility/restoration WO 01/41558Oilseed rape RT73 Glyphosate resistance WO 02/36831 Cotton CE43-67BInsect resistance (Cry1Ab) WO 2006/128573 Cotton CE46-02A Insectresistance (Cry1Ab) WO 2006/128572 Cotton CE44-69D Insect resistance(Cry1Ab) WO 2006/128571 Cotton 1143-14A Insect resistance (Cry1Ab) WO2006/128569 Cotton 1143-51B Insect resistance (Cry1Ab) WO 2006/128570Cotton T342-142 Insect resistance (Cry1Ab) WO 2006/128568 Cottonevent3006-210-23 Insect resistance (Cry1Ac) WO 2005/103266 CottonPV-GHGT07 (1445) Glyphosate tolerance US 2004-148666 Cotton MON88913Glyphosate tolerance WO 2004/072235 Cotton EE-GH3 Glyphosate toleranceWO 2007/017186 Cotton T304-40 Insect-resistance (Cry1Ab) WO2008/122406Cotton Cot202 Insect resistance (VIP3) US 2007-067868 Cotton LLcotton25Glufosinate resistance WO 2007/017186 Cotton EE-GH5 Insect resistance(Cry1Ab) WO 2008/122406 Cotton event 281-24-236 Insect resistance(Cry1F) WO 2005/103266 Cotton Cot102 Insect resistance (Vip3A) US2006-130175 Cotton MON 15985 Insect resistance (Cry1A/Cry2Ab) US2004-250317 Bent Grass Asr-368 Glyphosate tolerance US 2006-162007Brinjal EE-1 Insect resistance (Cry1Ac) WO 2007/091277

Among the diseases of plants or crops that can be controlled by themethod according to the invention, mention can be made of:

-   -   Powdery mildew diseases such as:        -   Blumeria diseases, caused for example by Blumeria graminis;        -   Podosphaera diseases, caused for example by Podosphaera            leucotricha;        -   Sphaerotheca diseases, caused for example by Sphaerotheca            fuliginea;        -   Uncinula diseases, caused for example by Uncinula necator;    -   Rust diseases such as:        -   Gymnosporangium diseases, caused for example by            Gymnosporangium sabinae;        -   Hemileia diseases, caused for example by Hemileia vastatrix;        -   Phakopsora diseases, caused for example by Phakopsora            pachyrhizi or Phakopsora meibomiae;        -   Puccinia diseases, caused for example by Puccinia recondite,            Puccinia graminis or Puccinia striiformis;        -   Uromyces diseases, caused for example by Uromyces            appendiculatus;    -   Oomycete diseases such as:        -   Albugo diseases caused for example by Albugo candida;        -   Bremia diseases, caused for example by Bremia lactucae;        -   Peronospora diseases, caused for example by Peronospora pisi            or P. brassicae;        -   Phytophthora diseases, caused for example by Phytophthora            infestans;        -   Plasmopara diseases, caused for example by Plasmopara            viticola;        -   Pseudoperonospora diseases, caused for example by            Pseudoperonospora humuli or Pseudoperonospora cubensis;        -   Pythium diseases, caused for example by Pythium ultimum;    -   Leafspot, leaf blotch and leaf blight diseases such as:        -   Alternaria diseases, caused for example by Alternaria            solani;        -   Cercospora diseases, caused for example by Cercospora            beticola;        -   Cladiosporum diseases, caused for example by Cladiosporium            cucumerinum;        -   Cochliobolus diseases, caused for example by Cochliobolus            sativus (Conidiaform: Drechslera, Syn: Helminthosporium) or            Cochliobolus miyabeanus;        -   Colletotrichum diseases, caused for example by            Colletotrichum lindemuthanium;        -   Cycloconium diseases, caused for example by Cycloconium            oleaginum;        -   Diaporthe diseases, caused for example by Diaporthe citri;        -   Elsinoe diseases, caused for example by Elsinoe fawcettii;        -   Gloeosporium diseases, caused for example by Gloeosporium            laeticolor;        -   Glomerella diseases, caused for example by Glomerella            cingulata;        -   Guignardia diseases, caused for example by Guignardia            bidwefli;        -   Leptosphaeria diseases, caused for example by Leptosphaeria            maculans; Leptosphaeria nodorum;        -   Magnaporthe diseases, caused for example by Magnaporthe            grisea;        -   Mycosphaerella diseases, caused for example by            Mycosphaerella graminicola; Mycosphaerella arachidicola;            Mycosphaerella fijiensis;        -   Phaeosphaeria diseases, caused for example by Phaeosphaeria            nodorum;        -   Pyrenophora diseases, caused for example by Pyrenophora            teres, or Pyrenophora tritici repentis;        -   Ramularia diseases, caused for example by Ramularia            collo-cygni, or Ramularia areola;        -   Rhynchosporium diseases, caused for example by            Rhynchosporium secalis;        -   Septoria diseases, caused for example by Septoria apii or            Septoria lycopercisi;        -   Typhula diseases, caused for example by Typhula incamata;        -   Venturia diseases, caused for example by Venturia            inaequalis;    -   Root, Sheath and stem diseases such as:        -   Corticium diseases, caused for example by Corticium            graminearum;        -   Fusarium diseases, caused for example by Fusarium oxysporum;        -   Gaeumannomyces diseases, caused for example by            Gaeumannomyces graminis;        -   Rhizoctonia diseases, caused for example by Rhizoctonia            solani;        -   Sarocladium diseases caused for example by Sarocladium            oryzae;        -   Sclerotium diseases caused for example by Sclerotium oryzae;        -   Tapesia diseases, caused for example by Tapesia acuformis;        -   Thielaviopsis diseases, caused for example by Thielaviopsis            basicola;    -   Ear and panicle diseases such as:        -   Alternaria diseases, caused for example by Alternaria spp.;        -   Aspergillus diseases, caused for example by Aspergillus            flavus;        -   Cladosporium diseases, caused for example by Cladosporium            spp.;        -   Claviceps diseases, caused for example by Claviceps            purpurea;        -   Fusarium diseases, caused for example by Fusarium culmorum;        -   Gibberella diseases, caused for example by Gibberella zeae;        -   Monographella diseases, caused for example by Monographella            nivalis;    -   Smut and bunt diseases such as:        -   Sphacelotheca diseases, caused for example by Sphacelotheca            reiliana;        -   Tilletia diseases, caused for example by Tilletia caries;        -   Urocystis diseases, caused for example by Urocystis occulta;        -   Ustilago diseases, caused for example by Ustilago nuda;    -   Fruit rot and mould diseases such as:        -   Aspergillus diseases, caused for example by Aspergillus            flavus;        -   Botrytis diseases, caused for example by Botrytis cinerea;        -   Penicillium diseases, caused for example by Penicillium            expansum;        -   Rhizopus diseases caused by example by Rhizopus stolonifer        -   Sclerotinia diseases, caused for example by Sclerotinia            sclerotiorum;        -   Verticilium diseases, caused for example by Verticilium            alboatrum;    -   Seed and soilbome decay, mould, wilt, rot and damping-off        diseases:        -   Alternaria diseases, caused for example by Alternaria            brassicicola        -   Aphanomyces diseases, caused for example by Aphanomyces            euteiches        -   Ascochyta diseases, caused for example by Ascochyta lentis        -   Aspergillus diseases, caused for example by Aspergillus            flavus        -   Cladosporium diseases, caused for example by Cladosporium            herbarum        -   Cochliobolus diseases, caused for example by Cochliobolus            sativus (Conidiaform: Drechslera, Bipolaris Syn:            Helminthosporium);        -   Colletotrichum diseases, caused for example by            Colletotrichum coccodes;        -   Fusarium diseases, caused for example by Fusarium culmorum;        -   Gibberella diseases, caused for example by Gibberella zeae;        -   Macrophomina diseases, caused for example by Macrophomina            phaseolina        -   Monographella diseases, caused for example by Monographella            nivalis;        -   Penicillium diseases, caused for example by Penicillium            expansum        -   Phoma diseases, caused for example by Phoma lingam        -   Phomopsis diseases, caused for example by Phomopsis sojae;        -   Phytophthora diseases, caused for example by Phytophthora            cactorum;        -   Pyrenophora diseases, caused for example by Pyrenophora            graminea        -   Pyricularia diseases, caused for example by Pyricularia            oryzae;        -   Pythium diseases, caused for example by Pythium ultimum;        -   Rhizoctonia diseases, caused for example by Rhizoctonia            solani;        -   Rhizopus diseases, caused for example by Rhizopus oryzae        -   Sclerotium diseases, caused for example by Sclerotium            rolfsii;        -   Septoria diseases, caused for example by Septoria nodorum;        -   Typhula diseases, caused for example by Typhula incarnata;        -   Verticillium diseases, caused for example by Verticillium            dahliae;    -   Canker, broom and dieback diseases such as:        -   Nectria diseases, caused for example by Nectria galligena;    -   Blight diseases such as:        -   Monilinia diseases, caused for example by Monilinia laxa;    -   Leaf blister or leaf curl diseases such as:        -   Exobasidium diseases caused for example by Exobasidium            vexans        -   Taphrina diseases, caused for example by Taphrina deformans;    -   Decline diseases of wooden plants such as:        -   Esca diseases, caused for example by Phaemoniella            clamydospora;        -   Eutypa dyeback, caused for example by Eutypa lata;        -   Ganoderma diseases caused for example by Ganoderma            boninense;        -   Rigidoporus diseases caused for example by Rigidoporus            lignosus    -   Diseases of Flowers and Seeds such as        -   Botrytis diseases caused for example by Botrytis cinerea;    -   Diseases of Tubers such as        -   Rhizoctonia diseases caused for example by Rhizoctonia            solani;        -   Helminthosporium diseases caused for example by            Helminthosporium solani;    -   Club root diseases such as        -   Plasmodiophora diseases, cause for example by Plamodiophora            brassicae.    -   Diseases caused by Bacterial Organisms such as        -   Xanthomonas species for example Xanthomonas campestris pv.            oryzae;        -   Pseudomonas species for example Pseudomonas syringae pv.            lachrymans;        -   Erwinia species for example Erwinia amylovora.

The composition according to the invention may also be used againstfungal diseases liable to grow on or inside timber. The term “timber”means all types of species of wood, and all types of working of thiswood intended for construction, for example solid wood, high-densitywood, laminated wood, and plywood. The method for treating timberaccording to the invention mainly consists in contacting one or morecompounds according to the invention or a composition according to theinvention; this includes for example direct application, spraying,dipping, injection or any other suitable means.

The dose of active compound usually applied in the method of treatmentaccording to the invention is generally and advantageously from 10 to800 g/ha, preferably from 50 to 300 g/ha for applications in foliartreatment. The dose of active substance applied is generally andadvantageously from 2 to 200 g per 100 kg of seed, preferably from 3 to150 g per 100 kg of seed in the case of seed treatment.

It is clearly understood that the doses indicated herein are given asillustrative examples of the method according to the invention. A personskilled in the art will know how to adapt the application doses, notablyaccording to the nature of the plant or crop to be treated.

The compounds or mixtures according to the invention can also be usedfor the preparation of composition useful to curatively or preventivelytreat human or animal fungal diseases such as, for example, mycoses,dermatoses, trichophyton diseases and candidiases or diseases caused byAspergillus spp., for example Aspergillus fumigatus.

The various aspects of the invention will now be illustrated withreference to the following table of compound examples and the followingpreparation or efficacy examples.

Table 1 illustrates in a non-limiting manner examples of compounds offormula (I) wherein Z³ is hydrogen, according to the invention:

In table 1, unless otherwise specified, M+H (Apcl+) means the molecularion peak plus 1 a.m.u. (atomic mass unit) as observed in massspectroscopy via positive atmospheric pressure chemical ionisation.

In table 1, the logP values were determined in accordance with EECDirective 79/831 Annex V.A8 by HPLC (High Performance LiquidChromatography) on a reversed-phase column (C 18), using the methoddescribed below:

Temperature: 40° C.; Mobile phases: 0.1% aqueous formic acid andacetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile.

Calibration was carried out using unbranched alkan-2-ones (comprising 3to 16 carbon atoms) with known logP values (determination of the logPvalues by the retention times using linear interpolation between twosuccessive alkanones). lambda-max-values were determined usingUV-spectra from 200 nm to 400 nm and the peak values of thechromatographic signals.

TABLE 1   Example   A   T   Z³   n

  Q¹   B   logP Mass (M + H) 1

O H 0 — — 2-methylphenyl 2.71 316 2

O H 0 — — 2-methylphenyl 3.19 313 3

O H 0 — — 2-methylphenyl 3.73 298 4

O H 0 — — 2-methylphenyl 3.06 330 5

O H 0 — — 2-methylphenyl 3.37 368 6

O H 0 — — 2-methylphenyl 3.21 352 7

S H 0 — — 2-methylphenyl 3.81 368 8

O H 0 — — 3,4-dimethylphenyl 3.87 382 9

O H 0 — — 3,4-dimethylphenyl 3.64 366 10

O H 0 — — 3,5-dimethylphenyl 3.23 330 11

O H 0 — — 3,5-dimethylphenyl 3.62 344 12

O H 0 — — 3,5-dimethylphenyl 4.34 312 13

O H 0 — — 3,5-dimethylphenyl 3.55 424 14

O H 0 — — 3,5-dimethylphenyl 3.09 343 15

O H 0 — — 3,5-dimethylphenyl 3.60 316 16

O H 0 — — 3,5-dimethylphenyl 4.59 344 17

O H 0 — — 3,5-dimethylphenyl 3.71 316 18

O H 0 — — 3,5-dimethylphenyl 3.55 376 19

O H 0 — — 3,5-dimethylphenyl 3.44 332 20

O H 0 — — 3,5-dimethylphenyl 3.67 344 21

O H 0 — — 3,5-dimethylphenyl 3.73 335 22

O H 0 — — 3,5-dimethylphenyl 4.59 399 23

O H 0 — — 3,5-dimethylphenyl 4.86 369 24

O H 0 — — 3,5-dimethylphenyl 3.85 380 25

O H 0 — — 3,5-dimethylphenyl 4.49 349 26

O H 0 — — 3,5-dimethylphenyl 4.51 393 27

O H 0 — — 3,5-dimethylphenyl 3.44 329 28

O H 0 — — 3,5-dimethylphenyl 4.06 349 29

O H 0 — — 3,5-dimethylphenyl 3.25 315 30

O H 0 — — 3,5-dimethylphenyl 3.71 366 31

O H 0 — — 3,5-dimethylphenyl 3.87 332 32

O H 0 — — 3,5-dimethylphenyl 4.34 346 33

O H 0 — — 3,5-dimethylphenyl 4.93 390 34

O H 0 — — 3,5-dimethylphenyl 4.27 383 35

O H 0 — — 3,5-dimethylphenyl 4.21 426 36

O H 0 — — 2-chlorophenyl 2.89 336 37

O H 0 — — 2-chlorophenyl 3.19 350 38

O H 0 — — 2-chlorophenyl 3.29 333 39

O H 0 — — 2-chlorophenyl 3.89 318 40

O H 0 — — 2-chlorophenyl 3.48 388 41

O H 0 — — 2-chlorophenyl 3.31 372 42

S H 0 — — 2-chlorophenyl 4.00 388 43

O H 0 — — 3-chlorophenyl 3.31 350 44

O H 0 — — 3-chlorophenyl 2.94 336 45

O H 0 — — 3-chlorophenyl 3.48 333 46

O H 0 — — 3-chlorophenyl 4.04 318 47

O H 0 — — 3-chlorophenyl 3.60 388 48

O H 0 — — 3-chlorophenyl 3.39 372 49

S H 0 — — 3-chlorophenyl 4.06 388 50

S H 0 — — 3-chlorophenyl 4.31 404 51

O H 0 — — 4-chlorophenyl 2.98 336 52

O H 0 — — 4-chlorophenyl 3.51 333 53

O H 0 — — 4-chlorophenyl 4.04 318 54

O H 0 — — 4-chlorophenyl 3.35 350 55

O H 0 — — 4-chlorophenyl 3.67 388 56

O H 0 — — 4-chlorophenyl 3.46 372 57

S H 0 — — 4-chlorophenyl 4.16 388 58

O H 0 — — 1,3-benzodioxol-5-yl 3.33 328 59

O H 0 — — 1,3-benzodioxol-5-yl 2.73 360 60

O H 0 — — 1,3-benzodioxol-5-yl 2.44 346 61

O H 0 — — 2,3-dihydro-1,4- benzodioxin-6-yl 2.82 357 62

O H 0 — — 2,3-dihydro-1,4- benzodioxin-6-yl 3.25 342 63

O H 0 — — 2,3-dihydro-1,4- benzodioxin-6-yl 2.66 374 64

O H 0 — — 2,3-dihydro-1,4- benzodioxin-6-yl 2.39 360 65

O H 0 — — 2,3-dihydro-1,4- benzodioxin-6-yl 2.75 396 66

O H 0 — — 2,3-dihydro-1,4- benzodioxin-6-yl 2.99 412 67

O H 0 — — 3,5-dimethoxyphenyl 2.84 376 68

O H 0 — — 3,5-dimethoxyphenyl 2.56 362 69

O H 0 — — 3,5-dimethoxyphenyl 3.02 359 70

O H 0 — — 3,5-dimethoxyphenyl 3.48 344 71

O H 0 — — 2,3-dichlorophenyl 4.29 352 72

O H 0 — — 2,3-dichlorophenyl 3.62 384 73

O H 0 — — 2,3-dichlorophenyl 3.25 370 74

O H 0 — — 2,3-dichlorophenyl 3.73 367 75

O H 0 — — 2,4-dichlorophenyl 3.60 386 76

O H 0 — — 2,4-dichlorophenyl 3.39 370 77

O H 0 — — 2,4-dichlorophenyl 3.89 367 78

O H 0 — — 2,4-dichlorophenyl 3.83 384 79

O H 0 — — 2,4-dichlorophenyl 4.54 352 80

O H 0 — — 2,4-dichlorophenyl 4.06 422 81

O H 0 — — 2,4-dichlorophenyl 3.87 406 82

O H 0 — — 2,5-dichlorophenyl 3.67 384 83

O H 0 — — 2,5-dichlorophenyl 3.29 370 84

O H 0 — — 2,5-dichlorophenyl 4.36 352 85

O H 0 — — 2,5-dichlorophenyl 3.78 367 86

O H 0 — — 2-bromophenyl 3.96 362 87

O H 0 — — 2-bromophenyl 3.25 394 88

O H 0 — — 2-bromophenyl 2.99 380 89

O H 0 — — 2-bromophenyl 3.35 377 90

O H 0 — — 2-bromophenyl 3.55 432 91

O H 0 — — 2-bromophenyl 3.39 416 92

S H 0 — — 2-bromophenyl 3.92 432 93

O H 0 — — 3-bromophenyl 4.11 362 94

O H 0 — — 3-bromophenyl 3.44 394 95

O H 0 — — 3-bromophenyl 3.06 380 96

O H 0 — — 3-bromophenyl 3.71 432 97

O H 0 — — 3-bromophenyl 3.51 416 98

S H 0 — — 3-bromophenyl 4.16 432 99

O H 0 — — 4-bromophenyl 3.11 380 100

O H 0 — — 4-bromophenyl 4.16 362 101

O H 0 — — 4-bromophenyl 3.64 377 102

O H 0 — — 4-bromophenyl 3.51 394 103

O H 0 — — 4-bromophenyl 3.78 432 104

O H 0 — — 4-bromophenyl 3.60 416 105

S H 0 — — 4-bromophenyl 4.29 432 106

O H 0 — — 3,4,5-trimethoxyphenyl 2.21 392 107

O H 0 — — 3,4,5-trimethoxyphenyl 2.64 389 108

O H 0 — — 3,4,5-trimethoxyphenyl 3.04 374 109

O H 0 — — 3,4,5-trimethoxyphenyl 2.49 406 110

O H 0 — — 3-phenoxyphenyl 4.16 391 111

O H 0 — — 3-phenoxyphenyl 4.65 376 112

O H 0 — — 3-phenoxyphenyl 3.96 408 113

O H 0 — — 3-phenoxyphenyl 3.60 394 114

O H 0 — — 3-phenoxyphenyl 4.18 446 115

O H 0 — — 3-phenoxyphenyl 3.99 430 116

O H 0 — — 3-iodophenyl 4.36 410 117

O H 0 — — 2-naphthyl 3.58 366 118

O H 0 — — 2-naphthyl 3.21 352 119

O H 0 — — 2-naphthyl 3.76 349 120

O H 0 — — 2-naphthyl 4.39 334 121

O H 0 — — 2-naphthyl 3.87 404 122

O H 0 — — 2-naphthyl 3.69 388 123

S H 0 — — 2-naphthyl 4.36 404 124

O H 0 — — 5-bromo-2-thienyl 3.13 .86 125

O H 0 — — 5-bromo-2-thienyl 3.51 400 126

O H 0 — — 5-bromo-2-thienyl 3.67 383 127

O H 0 — — 5-bromo-2-thienyl 4.29 368 128

O H 0 — — 5-bromo-2-thienyl 3.55 400 129

O H 1 —CH₂— — phenyl 2.54 316 130

O H 1 —CH₂— — phenyl 3.11 313 131

O H 1 —CH₂— — phenyl 2.92 330 132

O H 1 —CH₂— — phenyl 3.58 298 133

O H 1 —CH₂— — phenyl 3.17 351 134

O H 1 —CH₂— — phenyl 3.09 352 135

O H 1 —CH(Et)— — phenyl 3.87 396 136

O H 1 —CH(Et)— — phenyl 3.59 380 137

O H 1 —CH(Me)— — phenyl 3.59 382 138

O H 1 —CH(Me)— — phenyl 3.39 366 139

S H 1 —CH(Me)— — phenyl 4.14 382 140

S H 1 —CH(Et)— — phenyl 4.39 396 141

O H 1 —CH₂— — 2-methylphenyl 3.87 312 142

O H 1 —CH₂— — 2-methylphenyl 3.50 365 143

O H 1 —CH₂— — 3-methylphenyl 3.96 312 144

O H 1 —CH₂— — 3-methylphenyl 3.44 366 145

O H 1 —CH₂— — 3-methylphenyl 3.57 365 146

O H 1 —CH₂— — 4-methylphenyl 3.99 312 147

O H 1 —CH₂— — 4-methylphenyl 3.46 366 148

O H 1 —CH₂— — 4-methylphenyl 3.59 365 149

O H 1 —CH₂— O 4-methylphenyl 3.55 398 150

O H 1 —CH₂— O 4-methylphenyl 3.35 382 151

O H 1 —CH₂— — 3-fluorophenyl 3.19 369 152

O H 1 —CH₂— — 3-fluorophenyl 3.59 316 153

O H 1 —CH₂— — 3-fluorophenyl 3.13 370 154

O H 1 —CH₂— — 4-fluorophenyl 3.21 369 155

O H 1 —CH₂— — 4-fluorophenyl 3.57 316 156

O H 1 —CH₂— — 4-fluorophenyl 3.11 370 157

O H 1 —CH₂— — 2-methoxyphenyl 3.17 382 158

O H 1 —CH₂— — 2-methoxyphenyl 3.63 328 159

O H 1 —CH₂— — 2-methoxyphenyl 3.33 381 160

S H 1 —CH₂— — 2-methoxyphenyl 3.87 398 161

O H 1 —CH(Et)— — 2-chlorophenyl 4.44 430 162

O H 1 —CH(Et)— — 2-chlorophenyl 4.13 414 163

O H 1 —CH(Me)— — 2-chlorophenyl 3.72 400 164

O H 1 —CH(Me)— — 2-chlorophenyl 4.06 416 165

S H 1 —CH(Et)— — 2-chlorophenyl 4.95 430 166

S H 1 —CH(Me)— — 2-chlorophenyl 4.53 416 167

O H 1 —CH₂— — 3-(trifluoromethyl) phenyl 3.70 419 168

O H 1 —CH₂— — 3-(trifluoromethyl) phenyl 4.06 366 169

O H 1 —CH₂— — 3-(trifluoromethyl) phenyl 3.59 420 170

O H 1 —CH₂— — 1-naphthyl 3.76 401 171

O H 1 —CH₂— — 1-naphthyl 3.65 402 172

O H 1 —CH₂— O 2-naphthyl 3.87 434 173

O H 1 —CH₂— O 2-naphthyl 3.68 418 174

O H 2 —CH₂CH₂— — phenyl 3.44 327 175

O H 2 —CH₂CH₂— — phenyl 3.92 312 176

O H 2 —CH₂CH₂— — phenyl 3.25 344 177

O H 2 —CH₂CH₂— — phenyl 3.37 366 178

O H 2 —CH₂CH₂— — phenyl 3.52 365 179

S H 2 —CH₂CH₂— — phenyl 4.06 382 180

O H 2 —CH₂CH₂— O 3,5-dimethylphenyl 4.11 426 181

O H 2 —CH₂CH₂— O 3,5-dimethylphenyl 3.92 410 182

O H 2 —CH₂CH₂— O 2,4-difluorophenyl 3.29 418 183

O H 2 —CH₂CH₂— O 2,4-difluorophenyl 3.46 434 184

O H 2 —CH₂CH₂— O 2,4-dichlorophenyl 4.26 466 185

O H 2 —CH₂CH₂— O 2,4-dichlorophenyl 4.06 450 186

O H 2 —CH₂CH₂— O biphenyl-2-yl 4.39 474 187

O H 2 —CH₂CH₂— O biphenyl-2-yl 4.21 458 188

O H 2 —CH₂CH₂— O biphenyl-4-yl 4.49 474 189

O H 2 —CH₂CH₂— O biphenyl-4-yl 4.31 458 190

O H 2 —CH₂CH₂— O 2-naphthyl 4.09 448 191

O H 2 —CH₂CH₂— O 2-naphthyl 3.92 432 192

O H 2 —CH₂CH₂— — 2-thienyl 3.35 371 193

O H 2 —CH₂CH₂— — 2-thienyl 3.79 318 194

O H 2 —CH₂CH₂— — 2-thienyl 3.25 372 195

O H 2 —CH₂CH₂— O 5-(trifluoromethyl) pyridin-2-yl 3.74 467 196

O H 2 —CH₂CH₂— O 5-(trifluoromethyl) pyridin-2-yl 3.57 451

Table 2 illustrates in a non-limiting manner examples of compounds offormula (I) wherein Z³ is methyl, according to the invention:

In table 2, M+H (Apcl+) and logP are defined as in table 1.

TABLE 2 Mass Example formula (I) logP (M + H) 197

3.55 366 198

3.73 382 199

3.17 348

The following examples illustrate in a non-limiting manner thepreparation and efficacy of the compounds of formula (I) according tothe invention.

PREPARATION EXAMPLE 1 Preparation of(5-fluoro-1,3-dimethyl-1H-pyrazol-4-yl)[2-(2-methylphenyl)-piperidin-1-yl]methanone(Compound 1)

At room temperature, 91 mg (0.9 mmol) of triethylamine are dissolved in1.5 ml of dimethylformamide and stirred for 5 min. In this solution, aresuccessively added 190 mg (0.9 mmol) of 2-(2-methylphenyl)-piperidinehydrochloride, 142 mg (0.9 mmol) of5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxylic acid and 122 mg (0.9mmol) of 1-hydroxybenzotriazole. The solution is poured over a 12 mlcartridge containing 2 g of Si-DCC (loading of 0.98 mmol of DCC per gramof resin) and left overnight. The cartridge is then eluted by 10 ml ofdichloromethane and the organic phase is filtered over a basic aluminacartridge (2 g). The solvents are removed and the crude amide ispurified by column chromatography on silica gel (gradient heptane/ethylacetate) to yield 136 mg (45% yield) of pure(5-fluoro-1,3-dimethyl-1H-pyrazol-4-yl)[2-(2-methylphenyl)piperidin-1-yl]methanoneas an oil (M+H=316).

GENERAL PREPARATION EXAMPLE 2 Thionation of Amide of Formula (I) onChemspeed™ Apparatus

In a 13 ml Chemspeed™ vial is weighted 0.27 mmole of phosphorouspentasulfide (P₂S₅). 3 ml of a 0.18 molar solution of the amide (I)(0.54 mmol) in dioxane is added and the mixture is heated at reflux fortwo hours. The temperature is then cooled to 80° C. and 2.5 ml of waterare added. The mixture is heated at 80° C. for one more hour. 2 ml ofwater are then added and the reaction mixture is extracted twice by 4 mlof dichloromethane. The organic phase is deposited on a basic aluminacartridge (2 g) and eluted twice by 8 ml of dichloromethane. Thesolvents are removed and the crude thioamide derivative is analyzed byLCMS and NMR. Insufficiently pure compounds are further purified bypreparative LCMS.

EXAMPLE A In Vivo Preventive Test on Sphaerotheca fuliginea (Cucumber)

Solvent: 49 parts by weight of N,N-dimethylformamide

Emulsifier: 1 part by weight of Alkylarylpolyglycolether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for preventive activity, young plants are sprayed with thepreparation of active compound at the stated rate of application. Oneday after this treatment, the plants are inoculated with an aqueousspore suspension of Sphaerotheca fuliginea. Then the plants are placedin a greenhouse at approximately 23° C. and a relative atmospherichumidity of approximately 70%.

The test is evaluated 7 days after the inoculation. 0% means an efficacywhich corresponds to that of the untreated control, while an efficacy of100% means that no disease is observed.

Under these conditions, good (at least 70%) to total protection isobserved at a dose of 500 ppm of active ingredient with the followingcompounds from table A:

TABLE A Example Efficacy 1 95 4 95 6 95 7 100 9 93 10 95 11 95 30 100 3689 37 70 41 100 42 100 44 89 48 100 49 98 56 79 57 70 68 83 73 85 81 9482 79 83 94 88 94 91 95 92 100 95 91 97 96 98 100 115 95 122 94 123 88126 95 136 98 138 98 139 95 140 100 156 75 162 100 163 98 165 100 166100 196 70

EXAMPLE B In Vivo Preventive Test on Alternaria solani (Tomato)

Solvent: 49 parts by weight of N,N-dimethylformamide

Emulsifier: 1 part by weight of Alkylarylpolyglycolether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for preventive activity, young plants are sprayed with thepreparation of active compound at the stated rate of application. Oneday after this treatment, the plants are inoculated with an aqueousspore suspension of Alternaria solani. The plants remain for one day inan incubation cabinet at approximately 22° C. and a relative atmospherichumidity of 100%. Then the plants are placed in an incubation cabinet atapproximately 20° C. and a relative atmospheric humidity of 96%.

The test is evaluated 7 days after the inoculation. 0% means an efficacywhich corresponds to that of the untreated control while an efficacy of100% means that no disease is observed.

Under these conditions, good (at least 70%) to total protection isobserved at a dose of 500 ppm of active ingredient with the followingcompounds from table B:

TABLE B Example Efficacy 1 95 4 95 5 90 6 100 7 95 8 94 9 95 10 90 11100 34 90 36 95 37 95 40 95 41 100 42 100 43 95 44 95 47 100 48 100 49100 51 95 53 90 54 95 55 95 56 100 57 100 58 78 59 78 60 94 65 90 67 9568 80 71 80 72 95 73 95 76 90 80 100 81 100 82 95 83 95 86 90 87 95 8895 90 90 91 100 92 95 92 100 93 90 94 100 95 100 96 100 97 100 98 100 9990 103 80 104 100 105 100 110 78 112 94 113 94 114 90 115 100 116 78 11795 118 95 120 80 121 80 122 100 123 90 124 95 125 90 129 95 132 90 134100 135 95 136 100 137 100 138 100 139 95 140 100 141 90 142 94 143 80144 100 145 75 146 95 147 100 148 94 149 95 150 100 151 95 153 100 15489 155 78 156 100 157 100 160 90 162 100 163 100 164 89 165 90 166 100169 100 172 80 173 100 176 90 177 100 179 95 180 80 181 100 182 100 18395 184 95 185 100 186 80 187 95 188 70 189 100 190 90 191 100 194 100195 100 196 100

EXAMPLE C In Vivo Preventive Test on Pyrenophora teres (Barley)

Solvent: 49 parts by weight of N,N-dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for preventive activity, young plants are sprayed with thepreparation of active compound at the stated rate of application. Oneday after this treatment, the plants are inoculated with an aqueousspore suspension of Pyrenophora teres.

The plants remain for 48 hours in an incubation cabinet at 22° C. and arelative atmospheric humidity of 100%. Then the plants are placed in agreenhouse at a temperature of approximately 20° C. and a relativeatmospheric humidity of approximately 80%.

The test is evaluated 7-9 days after the inoculation. 0% means anefficacy which corresponds to that of the untreated control while anefficacy of 100% means that no disease is observed.

Under these conditions, good (at least 70%) to total protection isobserved at a dose of 500 ppm of active ingredient with the followingcompounds from table C:

TABLE C Example Efficacy 1 100 3 80 4 100 5 95 6 100 7 100 8 90 9 100 10100 11 100 12 90 30 100 34 100 36 100 37 95 40 95 41 100 42 100 43 10044 100 46 90 47 100 48 100 49 100 49 100 50 100 51 100 53 95 54 100 5580 56 100 57 100 59 70 60 80 64 95 65 100 67 90 68 95 70 80 71 80 72 9573 100 76 100 78 100 79 80 80 95 81 100 82 90 83 100 84 90 86 90 87 10088 95 90 95 91 100 92 100 93 95 94 70 95 95 96 100 97 100 98 100 99 100100 70 102 100 103 95 104 95 105 100 113 90 114 80 115 100 117 95 118100 120 70 121 90 122 100 123 100 124 100 125 80 129 100 131 100 132 90134 100 135 94 136 100 137 100 138 100 139 100 140 100 142 95 144 100145 80 147 100 148 95 149 95 150 100 153 100 154 100 156 100 157 100 15990 160 100 161 94 162 100 163 100 164 100 165 100 166 100 169 100 172 90173 95 176 95 177 95 179 100 180 80 181 100 182 100 183 100 184 100 18595 186 95 187 95 188 95 189 95 190 95 191 100 194 100 195 95 196 100

EXAMPLE D In Vivo Preventive Test on Venturia inaequalis (Apple Scab)

Solvent: 24.5 parts by weight of acetone

-   -   24.5 parts by weight of N,N-dimethylacetamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for preventive activity, young plants are sprayed with thepreparation of active compound at the stated rate of application. Afterthe spray coating has dried on, the plants are inoculated with anaqueous conidia suspension of the causal agent of apple scab (Venturiainaequalis) and then remain for 1 day in an incubation cabinet atapproximately 20° C. and a relative atmospheric humidity of 100%.

The plants are then placed in a greenhouse at approximately 21° C. and arelative atmospheric humidity of approximately 90%.

The test is evaluated 10 days after the inoculation. 0% means anefficacy which corresponds to that of the untreated control, while anefficacy of 100% means that no disease is observed.

Under these conditions, excellent (at least 98%) to total protection isobserved at a dose of 100 ppm of active ingredient with the followingcompounds from table D:

TABLE D Example Efficacy 1 99 10 100 11 100 30 100 54 98 67 100 136 100140 100 165 99

EXAMPLE E In Vivo Preventive Test on Uromyces appendiculatus (Bean Rust)

Solvent: 24.5 parts by weight of acetone

-   -   24.5 parts by weight of N,N-dimethylacetamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for preventive activity, young plants are sprayed with thepreparation of active compound at the stated rate of application. Afterthe spray coating has dried on, the plants are inoculated with anaqueous spore suspension of the causal agent of bean rust (Uromycesappendiculatus) and then remain for 1 day in an incubation cabinet atapproximately 20° C. and a relative atmospheric humidity of 100%.

The plants are then placed in a greenhouse at approximately 21° C. and arelative atmospheric humidity of approximately 90%.

The test is evaluated 10 days after the inoculation. 0% means anefficacy which corresponds to that of the untreated control, while anefficacy of 100% means that no disease is observed.

Under these conditions, good (at least 70%) to total protection isobserved at a dose of 100 ppm of active ingredient with the followingcompounds from table E:

TABLE E Example Efficacy 1 100 10 100 11 98 54 96 67 95 136 78 140 94165 73

EXAMPLE F In Vivo Preventive Test on Septoria tritici (Wheat)

Solvent: 49 parts by weight of N,N-dimethylacetamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound or active compound combination is mixed with thestated amounts of solvent and emulsifier, and the concentrate is dilutedwith water to the desired concentration.

To test for preventive activity, young plants are sprayed with thepreparation of active compound or active compound combination at thestated rate of application.

After the spray coating has been dried, the plants are sprayed with aspore suspension of Septoria tritici. The plants remain for 48 hours inan incubation cabinet at approximately 20° C. and a relative atmospherichumidity of approximately 100% and afterwards for 60 hours atapproximately 15° C. in a translucent incubation cabinet at a relativeatmospheric humidity of approximately 100%.

The plants are placed in the greenhouse at a temperature ofapproximately 15° C. and a relative atmospheric humidity ofapproximately 80%.

The test is evaluated 21 days after the inoculation. 0% means anefficacy which corresponds to that of the untreated control, while anefficacy of 100% means that no disease is observed.

Under these conditions, good (at least 70%) to total protection isobserved at a dose of 500 ppm of active ingredient with the followingcompounds from table F:

TABLE F Example Efficacy 1 100 4 100 10 70 11 100 30 100 36 80 37 80 4380 44 90 51 100 53 90 54 100 73 80 76 100 78 89 83 80 86 78 87 89 88 8995 100 117 90 118 100 136 100 140 100 162 100 176 70

EXAMPLE G In Vivo Preventive Test on Blumeria graminis (Barley)

Solvent: 49 parts by weight of N,N-dimethylacetamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound or active compound combination is mixed with thestated amounts of solvent and emulsifier, and the concentrate is dilutedwith water to the desired concentration.

To test for preventive activity, young plants are sprayed with thepreparation of active compound or active compound combination at thestated rate of application.

After the spray coating has been dried, the plants are dusted withspores of Blumeria graminis f. sp. hordei.

The plants are placed in the greenhouse at a temperature ofapproximately 18° C. and a relative atmospheric humidity ofapproximately 80% to promote the development of mildew pustules.

The test is evaluated 7 days after the inoculation. 0% means an efficacywhich corresponds to that of the untreated control, while an efficacy of100% means that no disease is observed.

Under these conditions, good (at least 70%) to total protection isobserved at a dose of 500 ppm of active ingredient with the followingcompounds from table G:

TABLE G Example Efficacy 1 89 4 78 10 88 11 80 30 100 53 70 54 70 95 100136 100 140 100 162 94

EXAMPLE H In Vivo Preventive Test on Leptosphaeria nodorum (Wheat)

Solvent: 49 parts by weight of N,N-dimethylacetamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound or active compound combination is mixed with thestated amounts of solvent and emulsifier, and the concentrate is dilutedwith water to the desired concentration.

To test for preventive activity, young plants are sprayed with thepreparation of active compound or active compound combination at thestated rate of application. After the spray coating has been dried, theplants are sprayed with a spore suspension of Leptosphaeria nodorum.

The plants remain for 48 hours in an incubation cabinet at approximately20° C. and a relative atmospheric humidity of approximately 100%.

The plants are placed in the greenhouse at a temperature ofapproximately 22° C. and a relative atmospheric humidity ofapproximately 80%.

The test is evaluated 8 days after the inoculation. 0% means an efficacywhich corresponds to that of the untreated control, while an efficacy of100% means that no disease is observed.

Under these conditions, good (at least 70%) to total protection isobserved at a dose of 500 ppm of active ingredient with the followingcompounds from table H:

TABLE H Example Efficacy 10 71 30 90 53 78 54 100 78 78 95 89 136 100140 93 162 90

EXAMPLE I In Vivo Preventive Test on Puccinia triticina (Wheat)

Solvent: 49 parts by weight of N,N-dimethylacetamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound or active compound combination is mixed with thestated amounts of solvent and emulsifier, and the concentrate is dilutedwith water to the desired concentration.

To test for preventive activity, young plants are sprayed with thepreparation of active compound or active compound combination at thestated rate of application. After the spray coating has been dried, theplants are sprayed with a spore suspension of Puccinia triticina.

The plants remain for 48 hours in an incubation cabinet at approximately20° C. and a relative atmospheric humidity of approximately 100%.

The plants are placed in the greenhouse at a temperature ofapproximately 20° C. and a relative atmospheric humidity ofapproximately 80%.

The test is evaluated 8 days after the inoculation. 0% means an efficacywhich corresponds to that of the untreated control, while an efficacy of100% means that no disease is observed.

Under these conditions, good (at least 70%) to total protection isobserved at a dose of 500 ppm of active ingredient with the followingcompounds from table I:

TABLE I Example Efficacy 10 88 11 100 30 100 53 71 54 100 95 71 162 100

EXAMPLE J In Vivo Preventive Test on Fusarium nivale (Wheat)

Solvent: 49 parts by weight of N,N-dimethylacetamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound or active compound combination is mixed with thestated amounts of solvent and emulsifier, and the concentrate is dilutedwith water to the desired concentration.

To test for preventive activity, young plants are sprayed with thepreparation of active compound or active compound combination at thestated rate of application.

After the spray coating has been dried, the plants are slightly injuredby using a sandblast and afterwards they are sprayed with a conidiasuspension of Fusarium nivale (var. majus).

The plants are placed in the greenhouse under a translucent incubationcabinet at a temperature of approximately 10° C. and a relativeatmospheric humidity of approximately 100%.

The test is evaluated 5 days after the inoculation. 0% means an efficacywhich corresponds to that of the untreated control, while an efficacy of100% means that no disease is observed.

Under these conditions, good (at least 70%) to total protection isobserved at a dose of 500 ppm of active ingredient with the followingcompounds from table J:

TABLE J Example Efficacy 10 88 11 83 30 100 53 100 54 71 95 100 136 86140 71

EXAMPLE K In Vivo Protective Test on Phakopsora pachyrhizi (Soybeans)

Solvent: 28.5 parts by weight of acetone

Emulsifier: 1.5 part by weight of polyoxyethylene alkyl phenyl ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated rate of application. Oneday after spraying, the plants are inoculated with an aqueous sporesuspension of the causal agent of soybean rust (Phakopsora pachyrhizi).The plants are then placed in a greenhouse at approximately 20° C. and arelative atmospheric humidity of approximately 80%.

The test is evaluated 11 days after the inoculation. 0% means anefficacy which corresponds to that of the control, while an efficacy of100% means that no disease is observed.

Under these conditions, high (at least 90%) is observed at a dose of 250ppm of active ingredient with the following compounds from table K:

TABLE K Example Efficacy 10 98 11 96 67 90

1. A compound of formula (I):

wherein A represents a carbo-linked, unsaturated or partially saturated,5-membered heterocyclyl group that can be substituted by up to fourgroups R that can be the same or different; T represents O or S; nrepresents 0, 1 or 2; Q¹ represents a bond; O; S; SO; or SO₂; Brepresents a phenyl ring that can be substituted by up to 5 groups Xwhich can be the same or different; a naphthyl ring that can besubstituted by up to 7 groups X which can be the same or different; or asaturated, partially saturated or unsaturated, monocyclic or fusedbicyclic 4-, 5-, 6-, 7-, 8-, 9-, 10-membered ring comprising from 1 upto 4 heteroaroms selected in the list consisting of N, O, S, that can besubstituted by up to 6 groups X which can be the same or different; Xrepresents a halogen atom; nitro; cyano; isonitrile; hydroxy; amino;sulfanyl; pentafluoro-λ⁶-sulfanyl; formyl; formyloxy; formylamino;substituted or non-substituted (hydroxyimino)-C₁-C₈-alkyl; substitutedor non-substituted (C₁-C₈-alkoxyimino)-C₁-C₈-alkyl; substituted ornon-substituted (C₂-C₈-alkenyloxyimino)-C₁-C₈-alkyl; substituted ornon-substituted (C₂-C₈-alkynyloxyimino)-C₁-C₈-alkyl; substituted ornon-substituted (benzyloxyimino)-C₁-C₈-alkyl; carboxy; carbamoyl;N-hydroxycarbamoyl; carbamate; substituted or non-substitutedC₁-C₈-alkyl; C₁-C₈-halogenoalkyl having 1 to 5 halogen atoms;substituted or non-substituted C₂-C₈-alkenyl; C₂-C₈-halogenoalkenylhaving 1 to 5 halogen atoms; substituted or non-substitutedC₂-C₈-alkynyl; C₂-C₈-halogenoalkynyl having 1 to 5 halogen atoms;substituted or non-substituted C₁-C₈-alkoxy; C₁-C₈-halogenoalkoxy having1 to 5 halogen atoms; substituted or non-substitutedC₁-C₈-alkylsulfanyl; C₁-C₈-halogenoalkylsulfanyl having 1 to 5 halogenatoms; substituted or non-substituted C₁-C₈-alkylsulfinyl;C₁-C₈-halogenoalkylsulfinyl having 1 to 5 halogen atoms; substituted ornon-substituted C₁-C₈-alkylsulfonyl; C₁-C₈-halogenoalkylsulfonyl having1 to 5 halogen atoms; substituted or non-substituted C₁-C₈-alkylamino;substituted or non-substituted di-C₁-C₈-alkylamino; substituted ornon-substituted C₂-C₈-alkenyloxy; C₂-C₈-halogenoalkenyloxy having 1 to 5halogen atoms; substituted or non-substituted C₃-C₈-alkynyloxy;C₂-C₈-halogenoalkynyloxy having 1 to 5 halogen atoms; substituted ornon-substituted C₃-C₇-cycloalkyl; C₃-C₇-halogenocycloalkyl having 1 to 5halogen atoms; substituted or non-substituted(C₃-C₇-cycloalkyl)-C₁-C₈-alkyl; substituted or non-substituted(C₃-C₇-cycloalkyl)-C₂-C₈-alkenyl; substituted or non-substituted(C₃-C₇-cycloalkyl)-C₂-C₈-alkynyl; substituted or non-substitutedtri(C₁-C₈)alkylsilyl; substituted or non-substitutedtri(C₁-C₈)alkylsilyl-C₁-C₈-alkyl; substituted or non-substitutedC₁-C₈-alkylcarbonyl; C₁-C₈-halogenoalkylcarbonyl having 1 to 5 halogenatoms; substituted or non-substituted C₁-C₈-alkylcarbonyloxy;C₁-C₈-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms; substitutedor non-substituted C₁-C₈-alkylcarbonylamino;C₁-C₈-halogenoalkyl-carbonylamino having 1 to 5 halogen atoms;substituted or non-substituted C₁-C₈-alkoxycarbonyl;C₁-C₈-halogenoalkoxycarbonyl having 1 to 5 halogen atoms; substituted ornon-substituted C₁-C₈-alkyloxycarbonyloxy;C₁-C₈-halogenoalkoxycarbonyloxy having 1 to 5 halogen atoms; substitutedor non-substituted C₁-C₈-alkylcarbamoyl; substituted or non-substituteddi-C₁-C₈-alkylcarbamoyl; substituted or non-substitutedC₁-C₈-alkylaminocarbonyloxy; substituted or non-substituteddi-C₁-C₈-alkylaminocarbonyloxy; substituted or non-substitutedN—(C₁-C₈-alkyl)hydroxy carbamoyl; substituted or non-substitutedC₁-C₈-alkoxycarbamoyl; substituted or non-substitutedN—(C₁-C₈-alkyl)-C₁-C₈-alkoxycarbamoyl; aryl that can be substituted byup to 6 groups Q which can be the same or different; C₁-C₈-arylalkylthat can be substituted by up to 6 groups Q which can be the same ordifferent; C₂-C₈-arylalkenyl that can be substituted by up to 6 groups Qwhich can be the same or different; C₂-C₈-arylalkynyl that can besubstituted by up to 6 groups Q which can be the same or different;aryloxy that can be substituted by up to 6 groups Q which can be thesame or different; arylsulfanyl that can be substituted by up to 6groups Q which can be the same or different; arylamino that can besubstituted by up to 6 groups Q which can be the same or different;C₁-C₈-arylalkyloxy that can be substituted by up to 6 groups Q which canbe the same or different; C₁-C₈-arylalkylsulfanyl that can besubstituted by up to 6 groups Q which can be the same or different; orC₁-C₈-arylalkylamino that can be substituted by up to 6 groups Q whichcan be the same or different; or two substituent X together with theconsecutive carbon atoms to which they are linked can form a 5- or6-membered, saturated carbocycle or saturated heterocycle, which can besubstituted by up to four groups Q which can be the same or different;Z¹ and Z² independently represent a hydrogen atom; a halogen atom;cyano; substituted or non-substituted C₁-C₈-alkyl; C₁-C₈-halogenoalkylhaving 1 to 5 halogen atoms; substituted or non-substitutedC₁-C₈-alkoxy; substituted or non-substituted C₁-C₈-alkylsulfanyl; orsubstituted or non-substituted C₁-C₈-alkoxycarbonyl; or two substituentsZ¹ and Z², together with the carbon atom to which they are linked canform a 3-, 4-, 5- or 6-membered saturated carbocycle that can besubstituted by up to four C₁-C₈-alkyl groups; Z³ represents a hydrogenatom; or substituted or non-substituted C₁-C₈-alkyl; Q independentlyrepresents a halogen atom; cyano; nitro; substituted or non-substitutedC₁-C₈-alkyl; C₁-C₈-halogenoalkyl having 1 to 9 halogen atoms that can bethe same or different; substituted or non-substituted C₁-C₈-alkoxy;C₁-C₈-halogenoalkoxy having 1 to 9 halogen atoms that can be the same ordifferent; substituted or non-substituted C₁-C₈-alkylsulfanyl;C₁-C₈-halogenoalkylsulfanyl having 1 to 9 halogen atoms that can be thesame or different; substituted or non-substituted tri(C₁-C₈)alkylsilyl;substituted or non-substituted tri(C₁-C₈)alkylsilyl-C₁-C₈-alkyl;substituted or non-substituted (C₁-C₈-alkoxyimino)-C₁-C₈-alkyl;substituted or non-substituted (benzyloxyimino)-C₁-C₈-alkyl; Rindependently represents hydrogen atom; halogen atom; nitro; cyano;hydroxy; amino; sulfanyl; pentafluoro-λ⁶-sulfanyl; substituted ornon-substituted (C₁-C₈-alkoxyimino)-C₁-C₈-alkyl; substituted ornon-substituted (benzyloxyimino)-C₁-C₈-alkyl; substituted ornon-substituted C₁-C₈-alkyl; C₁-C₈-halogenoalkyl having 1 to 5 halogenatoms; substituted or non-substituted C₂-C₈-alkenyl;C₂-C₈-halogenoalkenyl having 1 to 5 halogen atoms; substituted ornon-substituted C₂-C₈-alkynyl; C₂-C₈-halogenoalkynyl having 1 to 5halogen atoms; substituted or non-substituted C₁-C₈-alkoxy;C₁-C₈-halogenoalkoxy having 1 to 5 halogen atoms; substituted ornon-substituted C₁-C₈-alkylsulfanyl; C₁-C₈-halogenoalkylsulfanyl having1 to 5 halogen atoms; substituted or non-substitutedC₁-C₈-alkylsulfinyl; C₁-C₈-halogenoalkylsulfinyl having 1 to 5 halogenatoms; substituted or non-substituted C₁-C₈-alkylsulfonyl;C₁-C₈-halogenoalkylsulfonyl having 1 to 5 halogen atoms; substituted ornon-substituted C₁-C₈-alkylamino; substituted or non-substituteddi-C₁-C₈-alkylamino; substituted or non-substituted C₂-C₈-alkenyloxy;substituted or non-substituted C₃-C₈-alkynyloxy; substituted ornon-substituted C₃-C₇-cycloalkyl; C₃-C₇-halogenocycloalkyl having 1 to 5halogen atoms; substituted or non-substituted tri(C₁-C₈)alkylsilyl;substituted or non-substituted C₁-C₈-alkylcarbonyl;C₁-C₈-halogenoalkylcarbonyl having 1 to 5 halogen atoms; substituted ornon-substituted C₁-C₈-alkoxycarbonyl; C₁-C₈-halogenoalkoxycarbonylhaving 1 to 5 halogen atoms; substituted or non-substitutedC₁-C₈-alkylcarbamoyl; substituted or non-substituteddi-C₁-C₈-alkylcarbamoyl; phenoxy; phenylsulfanyl; phenylamino;benzyloxy; benzylsulfanyl; or benzylamino; as well as its salts,N-oxides, metal complexes, metalloid complexes and optically activeisomers provided that the following compounds are excluded:(2,5-dimethyl-3-furyl){2-[2-(3-methylphenyl)-2H-tetrazol-5-yl]piperidin-1-yl}methanone(5-bromo-2-furyl){2-[2-(3-bromophenyl)-2H-tetrazol-5-yl]piperidin-1-yl}methanone(5-bromo-2-furyl){2-[2-(3-chlorophenyl)-2H-tetrazol-5-yl]piperidin-1-yl}methanone(5-bromo-2-furyl){2-[2-(3-methoxyphenyl)-2H-tetrazol-5-yl]piperidin-1-yl}methanone(5-bromo-2-thienyl){2-[2-(3-chlorophenyl)-2H-tetrazol-5-yl]piperidin-1-yl}methanone(5-methyl-2-furyl){2-[2-(3-methylphenyl)-2H-tetrazol-5-yl]piperidin-1-yl}methanone{2-[2-(3,5-dichlorophenyl)-2H-tetrazol-5-yl]piperidin-1-yl}(5-methyl-2-furyl)methanone{2-[2-(3,5-dimethoxyphenyl)-2H-tetrazol-5-yl]piperidin-1-yl}(2-thienyl)methanone{2-[2-(3-bromophenyl)-2H-tetrazol-5-yl]piperidin-1-yl}(2-furyl)methanone{2-[2-(3-bromophenyl)-2H-tetrazol-5-yl]piperidin-1-yl}(2-thienyl)methanone{2-[2-(3-bromophenyl)-2H-tetrazol-5-yl]piperidin-1-yl}(4,5-dimethyl-2-furyl)methanone{2-[2-(3-bromophenyl)-2H-tetrazol-5-yl]piperidin-1-yl}(5-methyl-2-furyl)methanone{2-[2-(3-bromophenyl)-2H-tetrazol-5-yl]piperidin-1-yl}(5-methyl-2-thienyl)methanone{2-[2-(3-bromophenyl)-2H-tetrazol-5-yl]piperidin-1-yl}[5-(methylsulfanyl)-2-thienyl]methanone{2-[2-(3-chlorophenyl)-2H-tetrazol-5-yl]piperidin-1-yl}(1,2,3-thiadiazol-4-yl)methanone{2-[2-(3-chlorophenyl)-2H-tetrazol-5-yl]piperidin-1-yl}(1,3-dimethyl-1H-pyrazol-5-yl)methanone{2-[2-(3-chlorophenyl)-2H-tetrazol-5-yl]piperidin-1-yl}(1,5-dimethyl-1H-pyrazol-3-yl)methanone{2-[2-(3-chlorophenyl)-2H-tetrazol-5-yl]piperidin-1-yl}(2,4-dimethyl-1,3-thiazol-5-yl)methanone{2-[2-(3-chlorophenyl)-2H-tetrazol-5-yl]piperidin-1-yl}(2-methyl-3-furyl)methanone{2-[2-(3-chlorophenyl)-2H-tetrazol-5-yl]piperidin-1-yl}(3-furyl)methanone{2-[2-(3-chlorophenyl)-2H-tetrazol-5-yl]piperidin-1-yl}(4,5-dimethyl-2-furyl)methanone{2-[2-(3-chlorophenyl)-2H-tetrazol-5-yl]piperidin-1-yl}(4-methoxy-3-thienyl)methanone{2-[2-(3-chlorophenyl)-2H-tetrazol-5-yl]piperidin-1-yl}(4-methyl-1,3-thiazol-5-yl)methanone{2-[2-(3-chlorophenyl)-2H-tetrazol-5-yl]piperidin-1-yl}(5-methyl-1,2-oxazol-3-yl)methanone{2-[2-(3-chlorophenyl)-2H-tetrazol-5-yl]piperidin-1-yl}(5-methyl-2-thienyl)methanone{2-[2-(3-chlorophenyl)-2H-tetrazol-5-yl]piperidin-1-yl}[5-(methylsulfanyl)-2-thienyl]methanone{2-[2-(3-fluorophenyl)-2H-tetrazol-5-yl]piperidin-1-yl}(5-methyl-2-furyl)methanone{2-[2-(3-fluorophenyl)-2H-tetrazol-5-yl]piperidin-1-yl}(5-methyl-2-thienyl)methanone{2-[2-(3-methoxyphenyl)-2H-1-tetrazol-5-yl]piperidin-1-yl}(2-thienyl)methanone{2-[2-(3-methylphenyl)-2H-1-tetrazol-5-yl]piperidin-1-yl}(3-methyl-2-thienyl)methanone{2-[2-(3-methylphenyl)-2H-tetrazol-5-yl]piperidin-1-yl}(3-thienyl)methanone{2-[2-(3-methylphenyl)-2H-tetrazol-5-yl]piperidin-1-yl}(5-methyl-2-thienyl)methanone{2-[3-(3,4-dimethylphenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl}(3-methyl-2-thienyl)methanone{2-[3-(3-chlorophenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl}(2-furyl)methanone{2-[3-(3-chlorophenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl}(3-furyl)methanone{2-[3-(3-methoxyphenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl}(2-thienyl)methanone{2-[3-(3-methoxyphenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl}(5-methyl-2-thienyl)methanone{2-[3-(3-methylphenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl}(2-thienyl)methanone2-furyl{2-[2-(3-methylphenyl)-2H-tetrazol-5-yl]piperidin-1-yl}methanone2-furyl{2-[3-(3-methoxyphenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl}methanone2-furyl{2-[3-(3-methylphenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl}methanone3-(5-{1-[(5-bromo-2-thienyl)carbonyl]piperidin-2-yl}-2H-tetrazol-2-yl)benzonitrile3-(5-{1-[(5-methyl-2-thienyl)carbonyl]piperidin-2-yl}-1,2,4-oxadiazol-3-yl)benzonitrile3-(5-{1-[(5-methyl-2-thienyl)carbonyl]piperidin-2-yl}-2H-tetrazol-2-yl)benzonitrile3-[5-(1-{[5-(methylsulfanyl)-2-thienyl]carbonyl]piperidin-2-yl)-2H-tetrazol-2-yl}benzonitrile3-{5-[1-(2-furoyl)piperidin-2-yl]-2H-tetrazol-2-yl}benzonitrile3-{5-[1-(2-thienylcarbonyl)piperidin-2-yl]-2H-tetrazol-2-yl}benzonitrile3-{5-[1-(3-furoyl)piperidin-2-yl]-1,2,4-oxadiazol-3-yl}benzonitrile3-{5-[1-(3-furoyl)piperidin-2-yl]-2H-tetrazol-2-yl}benzonitrile3-{5-[1-(4,5-dimethyl-2-furoyl)piperidin-2-yl]-2H-tetrazol-2-yl}benzonitrile3-{5-[1-(5-methyl-2-furoyl)piperidin-2-yl]-2H-tetrazol-2-yl}benzonitrile3-furyl{2-[3-(3-methylphenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl}methanone 2.A compound according to claim 1 wherein A is selected in the listconsisting of: a heterocycle of formula (A¹)

wherein: R¹ to R³ that can be the same or different represent a hydrogenatom; a halogen atom; substituted or non-substituted C₁-C₅-alkyl;C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different; substituted or non-substituted C₁-C₅-alkoxy orC₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different; a heterocycle of formula (A²)

wherein: R⁴ to R⁶ that can be the same or different represent a hydrogenatom; a halogen atom; substituted or non-substituted C₁-C₅-alkyl;C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different; substituted or non-substituted C₁-C₅-alkoxy orC₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different; a heterocycle of formula (A³)

wherein: R⁷ represents a hydrogen atom; a halogen atom; substituted ornon-substituted C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different; substituted ornon-substituted C₁-C₈-alkoxy or C₁-C₅-halogenoalkoxy comprising up to 9halogen atoms that can be the same or different; R⁸ represents ahydrogen atom or a substituted or non-substituted C₁-C₅-alkyl; aheterocycle of formula (A⁴)

wherein: R⁹ to R¹¹ that can be the same or different represent ahydrogen atom; a halogen atom; substituted or non-substitutedC₁-C₅-alkyl; amino; substituted or non-substituted C₁-C₅-alkoxy;substituted or non-substituted C₁-C₅-alkylsulfanyl; C₁-C₅-halogenoalkylcomprising up to 9 halogen atoms that can be the same or different orC₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different; a heterocycle of formula (A⁵)

wherein: R¹² and R¹³ that can be the same or different represent ahydrogen atom; a halogen atom; substituted or non-substitutedC₁-C₅-alkyl; substituted or non-substituted C₁-C₅-alkoxy; amino;C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different or C₁-C₅-halogenoalkoxy comprising up to 9 halogenatoms that can be the same or different; R¹⁴ represents a hydrogen atom;a halogen atom; substituted or non-substituted C₁-C₅-alkyl; substitutedor non-substituted C₁-C₅-alkoxy; amino; C₁-C₅-halogenoalkyl comprisingup to 9 halogen atoms that can be the same or different orC₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different; a heterocycle of formula (A⁶)

wherein: R¹⁵ represents a hydrogen atom; a halogen atom; a cyano;substituted or non-substituted C₁-C₅-alkyl; substituted ornon-substituted C₁-C₈-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 9halogen atoms that can be the same or different or C₁-C₅-halogenoalkylcomprising up to 9 halogen atoms that can be the same or different; R¹⁶and R¹⁸ that can be the same or different represent a hydrogen atom; ahalogen atom; substituted or non-substituted C₁-C₅-alkoxycarbonyl;substituted or non-substituted C₁-C₅-alkyl; C₁-C₈-halogenoalkoxycomprising up to 9 halogen atoms that can be the same or different orC₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different; R¹⁷ represent a hydrogen atom or substituted ornon-substituted C₁-C₅-alkyl; a heterocycle of formula (A⁷)

wherein: R¹⁹ represents a hydrogen atom or a C₁-C₈-alkyl R²⁰ to R²² thatcan be the same or different represent a hydrogen atom; a halogen atom;substituted or non-substituted C₁-C₅-alkyl or C₁-C₅-halogenoalkylcomprising up to 9 halogen atoms that can be the same or different; aheterocycle of formula (A⁸)

wherein: R²³ represents a hydrogen atom; a halogen atom; substituted ornon-substituted C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different; R²⁴ represents ahydrogen atom or substituted or non-substituted C₁-C₅-alkyl orC₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different; a heterocycle of formula (A⁹)

wherein: R²⁵ represents a hydrogen atom; a halogen atom; substituted ornon-substituted C₁-C₈-alkyl or C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different; R²⁶ represents ahydrogen atom; substituted or non-substituted C₁-C₅-alkyl orC₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different; a heterocycle of formula (A¹⁰)

wherein: R²⁷ represents a hydrogen atom; a halogen atom; substituted ornon-substituted C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different; R²⁸ represents ahydrogen atom; a halogen atom; substituted or non-substitutedC₁-C₈-alkyl; C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms thatcan be the same or different; C₁-C₈-halogenoalkoxy comprising up to 9halogen atoms that can be the same or different; amino; substituted ornon-substituted C₁-C₅-alkylamino or substituted or non-substituteddi(C₁-C₅-alkyl)amino; a heterocycle of formula (A¹¹)

wherein: R²⁹ represents a hydrogen atom; a halogen atom; substituted ornon-substituted C₁-C₈-alkyl; substituted or non-substitutedC₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms thatcan be the same or different or C₁-C₈-halogenoalkyl comprising up to 9halogen atoms that can be the same or different; R³⁰ represents ahydrogen atom; a halogen atom; substituted or non-substitutedC₁-C₅-alkyl; C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms thatcan be the same or different; C₁-C₅-halogenoalkoxy comprising up to 9halogen atoms that can be the same or different; amino; substituted ornon-substituted C₁-C₅-alkylamino or substituted or non-substituteddi(C₁-C₈-alkyl)amino; a heterocycle of formula (A¹²)

wherein: R³¹ represents a hydrogen atom or a substituted ornon-substituted C₁-C₅-alkyl R³² represents a hydrogen atom; a halogenatom; substituted or non-substituted C₁-C₅-alkyl or C₁-C₅-halogenoalkylcomprising up to 9 halogen atoms that can be the same or different; R³³represents a hydrogen atom; a halogen atom; a nitro; substituted ornon-substituted C₁-C₈-alkyl; substituted or non-substitutedC₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms thatcan be the same or different or C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different; a heterocycle offormula (A¹³)

wherein: R³⁴ represents a hydrogen atom; a halogen atom; substituted ornon-substituted C₁-C₅-alkyl; substituted or non-substitutedC₃-C₅-cycloalkyl; C₁-C₈-halogenoalkyl comprising up to 9 halogen atomsthat can be the same or different; substituted or non-substitutedC₁-C₈-alkoxy; substituted or non-substituted C₂-C₅-alkynyloxy orC₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different; R³⁵ represents a hydrogen atom; a halogen atom;substituted or non-substituted C₁-C₈-alkyl; a cyano; substituted ornon-substituted C₁-C₅-alkoxy; substituted or non-substitutedC₁-C₅-alkylsulfanyl; C₁-C₈-halogenoalkyl comprising up to 9 halogenatoms that can be the same or different; C₁-C₈-halogenoalkoxy comprisingup to 9 halogen atoms that can be the same or different; amino;substituted or non-substituted C₁-C₅-alkylamino or substituted ornon-substituted di(C₁-C₅-alkyl)amino; R³⁶ represents a hydrogen atom orsubstituted or non-substituted C₁-C₅-alkyl; a heterocycle of formula(A¹⁴)

wherein: R³⁷ and R³⁸ that can be the same or different represent ahydrogen atom; a halogen atom; substituted or non-substitutedC₁-C₈-alkyl; C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms thatcan be the same or different; substituted or non-substitutedC₁-C₅-alkoxy or a substituted or non-substituted C₁-C₅-alkylsulfanyl;R³⁹ represents a hydrogen atom or substituted or non-substitutedC₁-C₈-alkyl; a heterocycle of formula (A¹⁵)

wherein: R⁴⁰ and R⁴¹ that can be the same or different represent ahydrogen atom; a halogen atom; substituted or non-substitutedC₁-C₈-alkyl or C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms thatcan be the same or different; a heterocycle of formula (A¹⁶)

wherein: R⁴² and R⁴³ that can be the same or different represent ahydrogen atom; a halogen atom; substituted or non-substitutedC₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms thatcan be the same or different or amino; a heterocycle of formula (A¹⁷)

wherein: R⁴⁴ and R⁴⁵ that can be the same or different represent ahydrogen atom; a halogen atom; substituted or non-substitutedC₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms thatcan be the same or different; a heterocycle of formula (A¹⁸)

wherein: R⁴⁷ represents a hydrogen atom; a halogen atom; substituted ornon-substituted C₁-C₈-alkyl or C₁-C₈-halogenoalkyl comprising up to 9halogen atoms that can be the same or different; R⁴⁶ represents ahydrogen atom; a halogen atom; substituted or non-substitutedC₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms thatcan be the same or different or substituted or non-substitutedC₁-C₅-alkylsulfanyl; a heterocycle of formula (A¹⁹)

wherein: R⁴⁹ and R⁴⁸ that can be the same or different represent ahydrogen atom; a halogen atom; substituted or non-substitutedC₁-C₈-alkyl; substituted or non-substituted C₁-C₈-alkoxy;C₁-C₈-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different or C₁-C₈-halogenoalkyl comprising up to 9 halogenatoms that can be the same or different; a heterocycle of formula (A²⁰)

wherein: R⁵⁰ and R⁵¹ that can be the same or different represent ahydrogen atom; a halogen atom; substituted or non-substitutedC₁-C₈-alkyl; substituted or non-substituted C₁-C₈-alkoxy;C₁-C₈-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different or C₁-C₈-halogenoalkyl comprising up to 9 halogenatoms that can be the same or different; a heterocycle of formula (A²¹)

wherein: R⁵² represents a hydrogen atom; a halogen atom; substituted ornon-substituted C₁-C₈-alkyl or C₁-C₈-halogenoalkyl comprising up to 9halogen atoms that can be the same or different. a heterocycle offormula (A²²)

wherein: R⁵³ represents a hydrogen atom; a halogen atom; substituted ornon-substituted C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different. a heterocycle offormula (A²³)

wherein: R⁵⁴ and R⁵⁶ that can be the same or different represent ahydrogen atom; a halogen atom; substituted or non-substitutedC₁-C₅-alkyl or C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms thatcan be the same or different; R⁵⁵ represents a hydrogen atom orsubstituted or non-substituted C₁-C₈-alkyl; a heterocycle of formula(A²⁴)

wherein: R⁵⁷ and R⁵⁹ that can be the same or different represent ahydrogen atom; a halogen atom; substituted or non-substitutedC₁-C₈-alkyl or C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms thatcan be the same or different; R⁵⁸ represents a hydrogen atom orsubstituted or non-substituted C₁-C₅-alkyl; a heterocycle of formula(A²⁵)

wherein: R⁶⁰ and R⁶¹ that can be the same or different represent ahydrogen atom; a halogen atom; substituted or non-substitutedC₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms thatcan be the same or different; R⁶² represents a hydrogen atom orsubstituted or non-substituted C₁-C₅-alkyl; a heterocycle of formula(A²⁶)

wherein: R⁶⁵ represents a hydrogen atom; a halogen atom; substituted ornon-substituted C₁-C₅-alkyl; substituted or non-substitutedC₃-C₅-cycloalkyl; C₁-C₅-halogenoalkyl comprising up to 9 halogen atomsthat can be the same or different; substituted or non-substitutedC₁-C₅-alkoxy; substituted or non-substituted C₂-C₅-alkynyloxy orC₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different; R⁶³ represents a hydrogen atom; a halogen atom;substituted or non-substituted C₁-C₈-alkyl; a cyano; substituted ornon-substituted C₁-C₅-alkoxy; substituted or non-substitutedC₁-C₅-alkylsulfanyl; C₁-C₅-halogenoalkyl comprising up to 9 halogenatoms that can be the same or different; C₁-C₅-halogenoalkoxy comprisingup to 9 halogen atoms that can be the same or different; amino;substituted or non-substituted C₁-C₅-alkylamino or di(C₁-C₅-alkyl)amino;R⁶⁴ represents a hydrogen atom or substituted or non-substitutedC₁-C₅-alkyl.
 3. A compound according to claim 2 wherein A is selected inthe list consisting of A²; A⁶; A¹⁰ and A¹³.
 4. A compound according toclaim 2 wherein A represents A¹³ wherein R³⁴ represents a substituted ornon-substituted C₁-C₈-alkyl, C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different; substituted ornon-substituted C₁-C₈-alkoxy; R³⁵ represents a hydrogen atom or ahalogen atom and R³⁶ represents a substituted or non-substitutedC₁-C₅-alkyl.
 5. A compound according to claim 2 wherein A represents A¹³wherein R³⁴ represents C₁-C₈-alkyl, C₁-C₅-halogenoalkyl comprising up to3 halogen atoms that can be the same or different; R³⁵ represents ahydrogen atom; a chlorine atom; or a fluorine atom; and R³⁶ represents amethyl.
 6. A compound according to claim 1 wherein T represents O.
 7. Acompound according to claim 1 wherein n represents 0 or
 1. 8. A compoundaccording to claim 1 wherein Q¹ represents a bond or an oxygen atom. 9.A compound according to claim 1 wherein B represents a substituted ornon-substituted phenyl ring; a substituted or non-substituted naphthylring; a substituted or non-substituted pyridyl ring; a substituted ornon-substituted thienyl ring; or a substituted or non-substitutedbenzothienyl ring.
 10. A compound according to claim 9 wherein Brepresents a substituted or non-substituted phenyl ring
 11. A compoundaccording to claim 9 wherein B represents a substituted ornon-substituted naphthyl ring.
 12. A compound according to claim 1wherein X independently represents a halogen atom; substituted ornon-substituted C₁-C₈-alkyl; C₁-C₈-halogenoalkyl comprising up to 9halogen atoms that can be the same or different; substituted ornon-substituted C₁-C₈-alkoxy or C₁-C₈-halogenoalkoxy comprising up to 9halogen atoms that can be the same or different; or wherein twoconsecutive substituents X together with the phenyl ring form asubstituted or non substituted 1,3-benzodioxolyl or 1,4-benzodioxanylring.
 13. A compound according to claim 1 wherein Z¹ and Z²independently represents a hydrogen atom, a halogen, substituted ornon-substituted C₁-C₈-alkyl or substituted or non-substitutedC₁-C₈-alkoxy.
 14. A compound according to claim 1 wherein Z³ representsa hydrogen atom.
 15. A fungicide composition comprising, as an activeingredient, an effective amount of a compound of formula (I) accordingto claim 1 and an agriculturally acceptable support, carrier or filler.16. A method for controlling phytopathogenic fungi of crops,characterized in that an agronomically effective and substantiallynon-phytotoxic quantity of a compound according to claim 1, is appliedto the soil where plants grow or are capable of growing, to the leavesand/or the fruit of plants or to the seeds of plants.
 17. A method forcontrolling phytopathogenic fungi of crops, characterized in that anagronomically effective and substantially non-phytotoxic quantity of afungicide composition according to claim 15, is applied to the soilwhere plants grow or are capable of growing, to the leaves and/or thefruit of plants or to the seeds of plants.